CN112079875A - 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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Abstract
The invention discloses an organic electroluminescent material, a preparation method thereof and an organic electroluminescent device, belonging to the technical field of luminescent materials1)(L2)x(L3)yThe general structural formula is as follows:
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.
Organic electroluminescent devices (OLEDs), as a novel flat panel display technology, are lightweight, ultra-thin, wide in viewing angle, flexible in display, and strong in anti-seismic performance, and gradually enter 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 an embodiment of the present invention is to provide an organic electroluminescent material to solve the problems in the background art.
Specifically, the embodiment of the invention provides an organic electroluminescent material which is an iridium metal complex and has a chemical formula of Ir (L)1)(L2)x(L3)yThe general structural formula is shown as formula I:
wherein x and y are both natural numbers, and x + y is 2.
Preferably, L2、L3Each independently is at least one of the following ligands:
in the formula, Ra、Rb、Rc、RdAnd ReAre respectively and independently 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 independently 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, L1Is 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 I2And/or L3Reacting with iridium trichloride to obtain a bridged ligand;
the bridging ligand B is reacted with the ligand L in the formula I1And 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): (0.5-10).
Specifically, the first electrode is an anode, the type of which is not particularly limited, and may be a conventional anode known to those skilled in the art, and more preferably is one of ITO (indium tin oxide), tin oxide, zinc oxide, and indium oxide, and the thickness of the first electrode is 10 to 500 nm. The second electrode is a cathode, the kind of which is not particularly limited, and is a conventional cathode known to those skilled in the art, and more preferably one of Al, Li, Na, K, Mg, Ca, Au, Ag, and Pb, and the thickness of the second electrode is 100 to 1000 nm.
The main material is preferably one or more of 4, 4'-N, N' -biphenyl dicarbazole (CBP), octahydroxyquinoline (Alq3), metal phenoxybenzothiazole compounds, polyfluorene, aromatic condensed rings and zinc complexes. The thickness of the light emitting layer is 10 to 500 nm.
In addition, the organic layer may further include other functional layers, and the other functional layers may be specifically selected from one or more of the following functional layers: a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a hole injection-hole transport functional layer (i.e., having both hole injection and hole transport functions), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), and an electron transport-electron injection functional layer (i.e., having both electron transport and electron injection functions).
The kind of each functional layer is not particularly limited, and may be a conventional functional layer known to those skilled in the art.
Preferably: the hole injection layer is one of 2-TNATA (namely N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine), phthalocyanine and porphyrin compounds, starburst triarylamine, a conductive polymer, an N-type semiconductive organic complex and a metal organic complex, and the thickness of the hole injection layer is 10-500 nm.
The hole transport layer is one of NPB (namely N, N '-diphenyl-N, N' - (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine), TPD (namely N, N '-diphenyl-N, N' - (3-methylphenyl) -1,1 '-biphenyl-4, 4' -diamine), PAPB (namely N, N '-bis (phenanthrene-9-yl) -N, N' -diphenyl benzidine) arylamine carbazole compound and indolocarbazole compound, and the thickness of the hole transport layer is 10-500 nm.
The hole blocking layer is one of BAlq, BCP and BPhen, and the thickness of the hole blocking layer is 10-500 nm.
The electron transport layer is one of Alq3, coumarin No. 6, triazole derivatives, azole derivatives, oxadiazole derivatives, imidazole derivatives, fluorenone derivatives and anthrone derivatives, and the thickness of the electron transport layer is 10-500 nm.
The electron injection layer is LiF, CsF or Li2O、Al2O3And MgO with a thickness of 0.1-10 nm.
In the embodiment of the present invention, the above light emitting layer and other various functional layers may be formed by a solution coating method and a vacuum deposition method. The solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, etc., but is not limited thereto.
The 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 beneficial effects that:
the organic electroluminescent material provided by the embodiment of the invention is prepared by combining the metallic iridium with the 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 requirements on conditions and high yield of target products, and solves the problems of high synthesis price and high synthesis process requirement 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 weighed3·3H2O (18.94mmol, 6.67g), ethylene glycol ethyl ether (150mL), and water (50mL) were added to the reaction system, respectively, under N2Heating 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 bridging ligand B-005 with a mass of 11.16g and a yield of 91%;
step 2: weighing bridging ligand B-005(8.48mmol, 11g), K2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50mL) were added to the reaction system separately under N2Adding ligand C-005 (shown in formula 5) (25.44mmol, 5.7g) under protection, heating to 120 deg.C, heating and refluxing for 24 hr, cooling to room temperature, vacuum filtering, leaching filter cake with ethanol and petroleum ether, oven drying at-0.1 MPa and 50 deg.C, and passing through silica gel column to obtain the final productLiquid is dried in a rotating way, and a target product I-005, namely the organic electroluminescent material (6.98mmol, 5.85g) is obtained, and the yield is 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, tested for 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 weighed3·3H2O (20.29mmol, 7.16g), ethylene glycol ethyl ether (150mL), and water (50mL) were added to the reaction system, respectively, under N2Heating 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-007 with a mass of 11.33g and a yield of 90.1%;
step 2: the bridged ligand B-007(8.86mmol, 11g), K was weighed2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50mL) were added to the reaction system separately under N2Adding ligand C-007 (shown in formula 6) (26.58mmol, 6.32g) under protection, heating to 120 deg.C, refluxing for 24 hr, cooling to room temperature, vacuum filtering, leaching filter cake with ethanol and petroleum ether, oven drying at-0.1 MPa and 50 deg.C, passing through silica gel column, and spin drying the obtained filtrate to obtain mesh productThe product, I-007, was obtained as an organic electroluminescent material (7.18mmol, 5.92g) in a yield of 40.6%.
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 823.85; the measured structure was substantially identical to the theoretical structure, tested for value 823.21.
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 weighed3·3H2O (14.63mmol, 5.15g), ethylene glycol ethyl ether (150mL), and water (50mL) were added to the reaction system, respectively, under N2Heating 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: weighing bridging ligand B-020(6.47mmol, 10g), K2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50mL) were added to the reaction system separately under N2Adding ligand C-020(19.41mmol, 4.35g) under protection, heating to 120 ℃, refluxing for 24h, cooling to room temperature, vacuum filtering, leaching filter cake with ethanol and petroleum ether, drying at-0.1 MPa and 50 ℃, passing through a silica gel column, and finally spin-drying the obtained filtrate to obtain the target product I-020, namely the organic electroluminescent deviceThe yield of the luminescent material (5.06mmol, 4.87g) was 39.2%.
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 961.33; the measured structure was substantially identical to the theoretical structure, tested for value 961.45.
Wherein the structural formula of the ligand C-020 is as follows:
material example 4
This example provides an organic electroluminescent material, whose chemical structural formula 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), IrCl were weighed3·3H2O (13.27mmol, 4.67g), ethylene glycol ethyl ether (150mL), and water (50mL) were added to the reaction system, respectively, under N2Heating 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-022 with the mass of 10g and the yield of 91%;
step 2: weighing bridging ligand B-022(6.03mmol, 10g), K2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50mL) were added to the reaction system separately under N2Adding ligand C-022(18.09mmol, 4.3g) under protection, heating to 120 deg.C, refluxing for 24h, cooling to room temperature, vacuum filtering, leaching the filter cake with ethanol and petroleum ether, oven drying at-0.1 MPa and 50 deg.C, passing through silica gel column, and spin drying the filtrate to obtain target product I-022, i.e. organic electroluminescent material (4.52mmol, 4.67g) with yield of 4.52mmol37.6％。
HPLC purity of the organic electroluminescent material: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 1031.15; the measured structure was substantially identical to the theoretical structure, tested for value 1031.32.
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 weighed3·3H2O (13.87mmol, 4.89g), ethylene glycol ethyl ether (150mL), and water (50mL) were added to the reaction system, respectively, under N2Heating 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), K2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50mL) were added to the reaction system separately under N2Adding ligand C-045(20.55mmol, 4.6g) 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-0.1 MPa and 50 ℃, passing through a silica gel column, and finally carrying out spin drying on 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 measured structure was substantially identical to the theoretical structure, tested for value 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 weighed3·3H2O (11.89mmol, 4.19g), ethylene glycol ethyl ether (150mL), and water (50mL) were added to the reaction system, respectively, under N2Heating 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: the bridged ligand B-064(5.77mmol, 11g), K was weighed2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50mL) were added to the reaction system separately under N2Adding ligand C-064(17.31mmol, 2.91g) 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-0.1 MPa 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: 99 percent.
Mass spectrum of the organic electroluminescent material: theoretical value 1085.38; the measured structure was substantially identical to the theoretical structure, tested for value 1085.41.
Wherein the structural formula of the ligand C-064 is as follows:
examples 7 to 18 of materials
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 invention content are similar to those of the material example 1 listed above, only corresponding ligands need to be replaced, so that the method is not exhaustive, and a plurality of organic electroluminescent materials are selected as the material examples 7-18 in the invention, and 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 |
| Material example 7 | I-001 | C30H30IrN3O | 641.20 | 641.81 |
| Material example 8 | I-008 | C38H46IrN3O | 753.33 | 753.02 |
| Material example 9 | I-018 | C46H46IrN3O | 849.33 | 849.11 |
| Material example 10 | I-027 | C60H66D8IrN3O | 1053.6 | 1053.54 |
| Material example 11 | I-035 | C52H60IrN5O | 963.44 | 963.31 |
| Material example 12 | I-038 | C54H64IrN5O | 991.47 | 991.36 |
| Material example 13 | I-042 | C58H64D8IrN5O | 1055.59 | 1055.62 |
| Material example 14 | I-050 | C54H62IrN3O | 961.45 | 961.33 |
| Material example 15 | I-054 | C52H52F6IrN3O | 1041.36 | 1041.22 |
| Material example 16 | I-057 | C60H66D8IrN3O | 1053.6 | 1053.51 |
| Material example 17 | I-062 | C56H44F2IrN3O3 | 1037.3 | 1037.38 |
| Material example 18 | I-070 | C56H40F6IrN3O3 | 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 layer of a hole injection layer, a hole transport layer, a composite layer of hole injection and hole transport technical layers, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, an electron transport layer, and a composite layer of electron injection technical layers, and at least one layer of the organic layer 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 put in distilled water for cleaning for 2 times, ultrasonically cleaned for 30 minutes, repeatedly cleaned for 2 times by distilled water, ultrasonically cleaned for 10 minutes, and ultrasonically cleaned by solvents such as isopropanol, acetone, methanol and the like in sequence after the cleaning by distilled water is finishedDrying after wave washing, transferring the product into a plasma cleaning machine for washing for 5 minutes, and then conveying the product into 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: 5.
(2) Under the same vacuum deposition conditions, tris (8-hydroxyquinoline) aluminum (Alq3,
) As an electron transport layer,
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 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 organic electroluminescent materials 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 fabricate a corresponding organic electroluminescent device.
Comparative device example 1
An organic electroluminescent device was fabricated by referring to the fabrication method provided in device example 1 above, except that the organic electroluminescent material I-005 (dopant material) in device example 1 above was replaced with the existing iridium metal complexThe material Ir (bty)2acac, wherein, Ir (bty)2The structural formula of acac is as follows:
experimental example:
the performance and the light emitting characteristics of the organic electroluminescent devices obtained in the device examples 1 to 18 and the device comparative example 1 were respectively tested under the same luminance conditions by using a KEITHLEY model 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the current efficiency and the light emitting life of the organic electroluminescent device (T95), and the specific test results are shown in table 2.
TABLE 2
As can be seen from Table 2 above, the results are shown in Ir (bty) as compared to that provided in comparative example 1 of the device2The 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 (9)
1. Organic electroluminescenceThe material is characterized in that the organic electroluminescent material is an iridium metal complex with a chemical formula of Ir (L)1)(L2)x(L3)yThe general structural formula is shown as formula I:
wherein x and y are both natural numbers, and x + y is 2.
2. An organic electroluminescent material according to claim 1, wherein L is2、L3Each independently is at least one of the following ligands:
in the formula, Ra、Rb、Rc、RdAnd ReAre respectively and independently one or more of hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C6-C18 aryl and C4-C12 aromatic heterocyclic group.
3. The organic electroluminescent material of claim 2, wherein the C1-C8 alkyl is independently one of a linear alkyl group, a branched alkyl group, and a cyclic alkyl group, which is unsubstituted or substituted with at least one substituent group.
4. An organic electroluminescent material according to claim 3, wherein the substituent group is one or more of methyl, ethyl, isopropyl, tert-butyl and isobutyl.
5. An organic electroluminescent material according to claim 1, wherein L is1Is one of the following ligands:
6. the organic electroluminescent material of claim 1, wherein the chemical structural formula of the organic electroluminescent material is any one of formulas I-001 to I-099:
7. a method for preparing an organic electroluminescent material as claimed in any one of claims 1 to 6, comprising the steps of:
the ligand L in the formula I2And/or L3Reacting with iridium trichloride to obtain a bridged ligand;
the bridging ligand B is reacted with the ligand L in the formula I1And carrying out reaction to obtain the organic electroluminescent material.
8. 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, wherein said organic layer comprises an organic electroluminescent material as claimed in any one of claims 1 to 6.
9. An organic electroluminescent device according to claim 8, 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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| WO2006000544A2 (en) * | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
| US20080058517A1 (en) * | 2006-09-06 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Electroluminescent complexes of IR(III) and devices |
| CN101652375A (en) * | 2007-02-14 | 2010-02-17 | 巴斯夫欧洲公司 | Electroluminescent metal complex |
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| WO2006000544A2 (en) * | 2004-06-28 | 2006-01-05 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent metal complexes with triazoles and benzotriazoles |
| US20080058517A1 (en) * | 2006-09-06 | 2008-03-06 | E. I. Du Pont De Nemours And Company | Electroluminescent complexes of IR(III) and devices |
| CN101652375A (en) * | 2007-02-14 | 2010-02-17 | 巴斯夫欧洲公司 | Electroluminescent metal complex |
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