CN111303213A - Phosphorescent iridium complex, preparation method thereof and organic electroluminescent device - Google Patents

Phosphorescent iridium complex, preparation method thereof and organic electroluminescent device Download PDF

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CN111303213A
CN111303213A CN202010294091.XA CN202010294091A CN111303213A CN 111303213 A CN111303213 A CN 111303213A CN 202010294091 A CN202010294091 A CN 202010294091A CN 111303213 A CN111303213 A CN 111303213A
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iridium complex
phosphorescent iridium
phosphorescent
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王辉
高旭
陈明
姜志远
于丹阳
张颖
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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    • 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
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Abstract

The invention discloses a phosphorescent iridium complex, a preparation method thereof and an organic electroluminescent device, belonging to the field of chemical synthesis and photoelectric materials, and having a structural general formula as follows:
Figure DDA0002451521320000011
in the formula, R1And R4Each independently represents n substituents, n being a natural number not greater than 4; r2And R3Each independently represents m substituents, m being a natural number not greater than 2; r5And R7Each independently is one or more of hydrogen, methyl, ethyl, isopropyl, aryl, monofluoromethyl, difluoromethyl, trifluoromethyl, tert-butyl and C3-C6 cycloalkyl; r6Independently hydrogen, deuterium, methyl, ethyl, isopropyl,Tert-butyl, halogen and cyano. The phosphorescent iridium complex is applied to an organic electroluminescent device as a doping material of a light-emitting layer, so that the driving voltage of the organic electroluminescent device can be obviously reduced, and the current efficiency and the phosphorescent service life of the organic electroluminescent device can be obviously improved.

Description

Phosphorescent iridium complex, preparation method thereof and organic electroluminescent device
Technical Field
The invention relates to the field of chemical synthesis and photoelectric materials, in particular to a phosphorescent iridium complex, a preparation method thereof and an organic electroluminescent device.
Background
Organic light-Emitting diodes (OLEDs) are highly desirable because they have excellent characteristics such as being ultra-thin, flexible, self-luminous, and wide in viewing angle. At present, the efficiency and the service life of the green light and blue light organic phosphorescent materials basically meet the requirements of industrial production, but high-performance red light phosphorescent materials still need to be developed.
Due to the lack of the current high-efficiency red light emitting materials, the organic electroluminescent materials are an important obstacle for restricting the application of the organic electroluminescent materials in full color display and other fields. Therefore, synthesizing a luminescent material with characteristics of low driving voltage, high current efficiency, easy light color adjustment, etc. becomes a very important research direction for designing novel organic phosphorescent luminescent materials at present.
Disclosure of Invention
It is an object of the embodiments of the present invention to provide a phosphorescent iridium complex to solve the problems in the background art.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
a phosphorescent iridium complex has a general structural formula of formula L:
Figure BDA0002451521310000011
in the formula, R1And R4Each independently represents n substituents, n being a natural number not greater than 4; r2And R3Each independently representm substituents, m being a natural number not greater than 2; r1、R2、R3And R4Each independently is one or more of hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C6-C18 aryl and C4-C12 aromatic heterocyclic group;
R5and R7Each independently is one or more of hydrogen, methyl, ethyl, isopropyl, aryl, monofluoromethyl, difluoromethyl, trifluoromethyl, tert-butyl and C3-C6 cycloalkyl;
R6independently one of hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, halogen and cyano.
Preferably, the C1-C8 alkyl is one of a linear alkyl, a branched alkyl and a cyclic alkyl which are unsubstituted or substituted by at least one first group; the first group is one or more of methyl, ethyl, isopropyl, tert-butyl and isobutyl.
Preferably, the C6 to C18 aryl groups are independently unsubstituted or substituted with at least one second group; the second group is one or more of deuterium, nitro, halogen, cyano and carbonyl.
Preferably, the C4 to C12 aromatic heterocyclic group is an unsubstituted or substituted aromatic heterocyclic group by at least one third group; the third group is one or more of deuterium, halogen, cyano and nitro.
Preferably, the halogen is fluorine.
Preferably, the chemical structural formula of the phosphorescent iridium complex is one of a formula L-001 to a formula L-108:
Figure BDA0002451521310000021
Figure BDA0002451521310000031
Figure BDA0002451521310000041
Figure BDA0002451521310000051
Figure BDA0002451521310000061
Figure BDA0002451521310000071
another objective of the embodiments of the present invention is to provide a method for preparing the above phosphorescent iridium complex, which includes the following steps:
reacting a reactant A with a general formula A with iridium trichloride to obtain a bridged ligand B;
reacting the bridging ligand B with a diketone derivative with a general formula of C to obtain the phosphorescent iridium complex;
Figure BDA0002451521310000072
Figure BDA0002451521310000081
preferably, the step of reacting the reactant a with the general formula a and iridium trichloride to obtain the bridged ligand B specifically comprises:
mixing a reactant A with a general formula of A, iridium trichloride, ethylene glycol ethyl ether and water, and then placing the mixture in a protective atmosphere for reaction to obtain a bridged ligand B.
Preferably, the step of reacting the bridging ligand B with a diketone derivative having a general formula C to obtain the phosphorescent iridium complex specifically includes:
and mixing the bridging ligand B, potassium carbonate and ethylene glycol ethyl ether, placing the mixture in a protective atmosphere at the temperature of 110-120 ℃, and adding a diketone derivative with the general formula of C for reaction to obtain the phosphorescent iridium complex.
The synthetic route of the preparation method is as follows:
Figure BDA0002451521310000082
another object of an embodiment of the present invention is 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 part or all of the organic layer includes the phosphorescent iridium complex.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the embodiment of the invention provides a novel phosphorescent iridium complex, and the preparation method of the phosphorescent iridium complex is simple and convenient to operate and low in cost; the phosphorescent iridium complex is applied to an organic electroluminescent device as a doping material of a light-emitting layer, so that the driving voltage of the organic electroluminescent device can be obviously reduced, and the current efficiency and the phosphorescent service life of the organic electroluminescent device can be obviously improved.
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.
Example 1
The embodiment provides a phosphorescent iridium complex, the chemical structural formula of which is formula L-001 in the summary of the invention, and the reaction route of the preparation method of the phosphorescent iridium complex is as follows:
Figure BDA0002451521310000091
the specific preparation method comprises the following steps:
step 1: reactant A-001(34.83mmol, 10g) and IrCl were weighed3·3H2O (13.93mmol, 4.90g), ethylene glycol ethyl ether (150ml), and water (50ml) were added to each ofReaction system in N2Heating and refluxing for 24h under protection, cooling to room temperature, separating out precipitate, vacuum filtering, sequentially eluting with anhydrous ethanol and petroleum ether, and oven drying to obtain bridging ligand B-001(6.24mmol, 10g) with yield of 91.47%;
step 2: weighing bridging ligand B-001(6.24mmol, 10g), K2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50ml) were added to the reaction system separately under N2Adding 2, 4-pentanedione (18.72mmol, 1.87g) 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 L-001, namely the phosphorescent iridium complex (5.90mmol, 5.10g), wherein the yield is 47.3%.
Elemental analysis of the phosphorescent iridium complex:
theoretical value C, 62.56%; h, 3.85%; f, 4.40%; ir, 22.25%; n, 3.24%; o, 3.70%;
test value C, 62.54%; h, 3.81%; f, 4.40%; ir, 22.24%; n, 3.23%; and O,3.72 percent.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 864.21; the measured structure was substantially identical to the theoretical structure, tested for value 863.98.
Example 2
The embodiment provides a phosphorescent iridium complex, the chemical structural formula of which is formula L-003 in the summary of the invention, and the reaction route of the preparation method of the phosphorescent iridium complex is as follows:
Figure BDA0002451521310000101
the specific preparation method comprises the following steps:
step 1: weighing reactant A-003(33.20mmol, 10g) and IrCl3·3H2O (13.28mmol, 4.68g), ethylene glycol ethyl ether (150ml) and water (50ml) were added to the reaction system separately under N2Heating and refluxing for 24h under protection, cooling to room temperature, and precipitatingPrecipitating the precipitate, vacuum filtering, sequentially eluting with anhydrous ethanol and petroleum ether, and oven drying to obtain bridging ligand B-003(6.03mmol, 10g) with yield of 90%;
step 2: weighing bridging ligand B-003(6.03mmol, 10g), K2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50ml) were added to the reaction system separately under N2Adding 2, 4-pentanedione (18.09mmol, 1.80g) 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 L-003, namely the phosphorescent iridium complex (5.90mmol, 5.27g), wherein the yield is 49%.
Elemental analysis of the phosphorescent iridium complex:
theoretical value C, 63.28%; h, 4.18%; f, 4.26%; ir, 21.55%; n, 3.14%; o, 3.59%;
test value C, 63.29%; h, 4.20%; f, 4.28%; ir, 21.54%; n, 3.13%; and O, 3.61%.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 892.25; the measured structure was substantially identical to the theoretical structure, tested for value 892.04.
Example 3
The example provides a phosphorescent iridium complex, the chemical structural formula of which is formula L-009 in the summary of the invention, and the reaction route of the preparation method of the phosphorescent iridium complex is as follows:
Figure BDA0002451521310000111
the specific preparation method comprises the following steps:
step 1: reaction A-009(33.2mmol, 10g) and IrCl were weighed3·3H2O (13.28mmol, 4.68g), ethylene glycol ethyl ether (150ml) and water (50ml) were added to the reaction system separately under N2Heating and refluxing for 24h under protection, cooling to room temperature, separating out precipitate, vacuum filtering, sequentially eluting with anhydrous ethanol and petroleum ether, and oven drying to obtain bridgeCatenin B-009(5.98mmol, 10g) in 90% yield;
step 2: the bridged ligand B-009(5.98mmol, 10g), K, was weighed2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50ml) were added to the reaction system separately under N2Adding 2, 4-pentanedione (17.94mmol, 1.79g) 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 L-009(6.08mmol, 5.48g), namely the phosphorescent iridium complex with the yield of 51%.
Elemental analysis of the phosphorescent iridium complex:
theoretical value C, 60.06%; h, 3.47%; f, 8.44%; ir, 21.36%; n, 3.11%; o, 3.56%;
test value C, 60.04%; h, 3.44%; f, 8.41%; ir, 21.31%; n, 3.10%; and O,3.52 percent.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 900.20; the measured structure was substantially identical to the theoretical structure, tested for value 899.97.
Example 4
The embodiment provides a phosphorescent iridium complex, the chemical structural formula of which is formula L-014 in the summary of the invention, and the reaction route of the preparation method of the phosphorescent iridium complex is as follows:
Figure BDA0002451521310000121
the specific preparation method comprises the following steps:
step 1: reaction A-014(30.38mmol, 10g), IrCl were weighed3·3H2O (12.15mmol, 4.28g), ethylene glycol ethyl ether (150ml) and water (50ml) were added to the reaction system separately under N2Heating and refluxing for 24h under protection, 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-014(5.48mmol, 9.7g) with yield of 90.23%;
step 2: the bridging ligand B-014(5.37mmol, 9.5g), K was weighed2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50ml) were added to the reaction system separately under N2Adding 3, 5-heptanedione (16.11mmol, 2.06g) 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 L-014(4.94mmol, 4.83g), namely the phosphorescent iridium complex, wherein the yield is 45%.
Elemental analysis of the phosphorescent iridium complex:
theoretical value C, 65.21%; h, 5.06%; f, 3.89%; ir, 19.69%; n, 2.87%; o, 3.28%;
test value C, 65.18%; h, 5.01%; f, 3.88%; ir, 19.68%; n, 2.88%; and O,3.29 percent.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 976.34; the measured structure was substantially identical to the theoretical structure, tested for value 976.21.
Example 5
The embodiment provides a phosphorescent iridium complex, the chemical structural formula of which is formula L-037 in the summary of the invention, and the reaction route of the preparation method of the phosphorescent iridium complex is as follows:
Figure BDA0002451521310000131
the specific preparation method comprises the following steps:
step 1: reactant A-037(34.44mmol, 10g), IrCl were weighed3·3H2O (13.78mmol, 4.85g), ethylene glycol ethyl ether (150ml) and water (50ml) were added to the reaction system respectively in N2Heating and refluxing for 24h under protection, cooling to room temperature, separating out precipitate, vacuum filtering, sequentially eluting with anhydrous ethanol and petroleum ether, and oven drying to obtain bridging ligand B-037(6.57mmol, 10.6g) with yield of 95.49%;
step 2: weighing bridging ligand B-037(6.20mmol, 10g), K2CO3(26mmol，3.60g) of ethylene glycol ethyl ether (50ml) was added to the reaction system separately under N2Adding 2,2,6, 6-tetramethyl-3, 5-heptanedione (18.6mmol, 3.42g) under protection, raising the temperature to 120 ℃, heating and refluxing for 24h, cooling to room temperature, carrying out suction filtration under reduced pressure, 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 L-037(6.68mmol, 6.38g), namely the phosphorescent iridium complex, wherein the yield is 54%.
Elemental analysis of the phosphorescent iridium complex:
theoretical value C, 64.20%; h, 5.39%; f, 3.98%; ir, 20.14%; n, 2.94%; o, 3.35%;
test value C, 64.18%; h, 5.41%; f, 3.97%; ir, 20.12%; n, 2.91%; and O,3.40 percent.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 954.35; the measured structure was substantially identical to the theoretical structure, tested for value 954.18.
Example 6
The embodiment provides a phosphorescent iridium complex, the chemical structural formula of which is formula L-068 in the summary of the invention, and the reaction route of the preparation method of the phosphorescent iridium complex is as follows:
Figure BDA0002451521310000141
the specific preparation method comprises the following steps:
step 1: reaction A-068(29.14mmol, 10g), IrCl were weighed3·H2O (11.66mol, 6.77g), ethylene glycol ethyl ether (150ml) and water (50ml) were added to the reaction system respectively in the presence of N2Heating and refluxing for 24h under protection, 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-068(5.26mmol, 9.6g) with yield of 90.3%;
step 2: the bridged ligand B-068(5.20mmol, 9.5g), K was weighed2CO3(26mmol, 3.60g) and ethylene glycol ethyl ether (50ml) were added to the reaction system separately under N2Adding 3, 7-diethyl-4, 6-nonanedione (15.6mmol, 3.31g) under protection, raising the temperature to 110 ℃, heating and refluxing for 24h, cooling to room temperature, carrying out vacuum filtration, leaching a filter cake with ethanol and petroleum ether, drying the filter cake at 50 ℃ under-0.1 MPa, passing through a silica gel column, and finally spin-drying the obtained filtrate to obtain a target product L-068(5.81mmol, 6.33g), namely the phosphorescent iridium complex, with the yield of 56%.
Elemental analysis of the phosphorescent iridium complex:
theoretical value C, 67.32%; h, 6.02%; f, 3.49%; ir, 17.66%; n, 2.57%; o, 2.94%;
test value C, 67.30%; h, 6.06%; f, 3.50%; ir, 17.65%; n, 2.59%; o,2.98 percent.
HPLC purity: 99 percent.
Mass spectrum: theoretical value 1088.42; the measured structure was substantially identical to the theoretical structure, tested for value 1088.46.
The synthetic routes and principles of the preparation methods of other compounds with the general structural formula of formula L in the summary of the invention are the same as those of the listed examples 1-6, so that the synthesis routes and principles are not exhaustive, and the invention selects a plurality of compounds (the formulas L-004, L-005, L-010, L-020, L-021, L-026, L-035, L-039, L-046, L-051, L-064, L-075, L-087 and L-094 in the summary of the invention) as examples, and the corresponding mass spectrum test values and molecular formulas are shown in the following table 1.
TABLE 1
Figure BDA0002451521310000151
Figure BDA0002451521310000161
The embodiment of the invention also provides an organic electroluminescent device prepared by adopting the phosphorescent iridium complex provided by the embodiment, wherein the organic electroluminescent device comprises a first electrode, a second electrode and at least one organic layer arranged between the first electrode and the second electrode.
The organic layer may include a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, and a light-emitting layer, and may also include an electron transport layer, an electron injection layer, a hole blocking layer, an electron blocking layer, and the like; the phosphorescent iridium complex provided by the above embodiment may be used as a dopant material in the light emitting layer.
The organic electroluminescent device mentioned in the embodiments of the present invention may be a top emission type, a bottom emission type, or a double-sided emission type depending on the material used. In addition, the phosphorescent iridium complex provided by the embodiment of the invention can also be used for organic electronic devices using a principle similar to that of an organic electroluminescent device, such as an organic solar cell, an organic photoconductor, an organic transistor, and the like.
Specifically, the method for producing the organic electroluminescent element described above can be referred to example 7.
Example 7
The embodiment provides a method for manufacturing an organic electroluminescent device, which includes the steps of:
coating with a thickness of
Figure BDA0002451521310000162
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, cleaned by distilled water, ultrasonically cleaned by solvents such as isopropanol, acetone, methanol and the like in sequence, dried, transferred into a plasma cleaning machine for cleaning for 5 minutes, and then sent into an evaporation machine for evaporation according to the following method:
(1) firstly, an ITO glass substrate (anode) is evaporated to a thickness of
Figure BDA0002451521310000163
N, N '-diphenyl-N, N' -di (1-naphthyl) -1,1 '-biphenyl-4, 4' -diamine (NPB) as a hole transport layer, and 4'-N, N' -biphenyl dicarbazole ("CBP") and the phosphorescent iridium complex having the structural formula L-001 provided in example 1 above were mixed-evaporated on the hole transport layer at a mass ratio of 95:5 as a light emitting layer.
(2) Under the same vacuum deposition condition, three (8-hydroxyl) is evaporated on the luminescent layer in sequenceQuinoline) aluminum (Alq3,
Figure BDA0002451521310000164
) As an electron transport layer,
Figure BDA0002451521310000173
As an electron injection layer,
Figure BDA0002451521310000174
The Al is used as a cathode, and the organic electroluminescent device can be obtained.
Referring to the method provided in example 7, phosphorescent iridium complexes having chemical structures of L-003, L-009, L-014, L-037, L-068, L-004, L-005, L-010, L-020, L-021, L-026, L-035, L-039, L-046, L-051, L-064, L-075, L-087, and L-094 are respectively selected to replace the phosphorescent iridium complex having the structural formula of L-001 as a doping material to be mixed with 4'-N, N' -biphenyldicarbazole ("CBP") as a host material in a mass ratio of 5:95 for evaporation, and a corresponding organic electroluminescent device is prepared.
Comparative example 1
This comparative example provides an organic electroluminescent device which was fabricated by a method different from that of example 7 only in that Ir (bty) was used2(acac) substitutes the phosphorescent iridium complex with the chemical structural formula of L-001 as a doping material to be mixed and evaporated with a main material 4'-N, N' -biphenyl dicarbazole ("CBP") according to the mass ratio of 5: 95. Wherein, Ir (bty)2(acac) has the structural formula:
Figure BDA0002451521310000171
the organic electroluminescent devices obtained in example 7 and comparative example 1 were subjected to the driving voltage, maximum emission peak Wavelength (WP), current efficiency (C.E), and T95 lifetime, respectively, and the test results are shown in table 2 below.
TABLE 2
Figure BDA0002451521310000172
Figure BDA0002451521310000181
As can be seen from Table 2 above, instead of using the existing Ir (bty)2Compared with the organic electroluminescent device prepared by taking the (acac) as the luminescent layer doping material, the organic electroluminescent device prepared by taking the phosphorescent iridium complex provided by the embodiment of the invention as the luminescent layer doping material has the advantages that the driving voltage is obviously reduced, and the current efficiency and the service life are obviously improved.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (10)

1. A phosphorescent iridium complex is characterized in that the structural general formula of the phosphorescent iridium complex is formula L:
Figure FDA0002451521300000011
in the formula, R1And R4Each independently represents n substituents, n being a natural number not greater than 4; r2And R3Each independently represents m substituents, m being a natural number not greater than 2; r1、R2、R3And R4Each independently is one or more of hydrogen, deuterium, halogen, cyano, nitro, C1-C8 alkyl, C1-C8 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C6-C18 aryl and C4-C12 aromatic heterocyclic group;
R5and R7Each independently is one or more of hydrogen, methyl, ethyl, isopropyl, aryl, monofluoromethyl, difluoromethyl, trifluoromethyl, tert-butyl and C3-C6 cycloalkyl;
R6independently one of hydrogen, deuterium, methyl, ethyl, isopropyl, tertiary butyl, halogen and cyano.
2. The phosphorescent iridium complex of claim 1, wherein the C1-C8 alkyl is independently one of a linear alkyl group, a branched alkyl group, a cyclic alkyl group, which is unsubstituted or substituted with at least one first group; the first group is one or more of methyl, ethyl, isopropyl, tert-butyl and isobutyl.
3. The phosphorescent iridium complex of claim 2 wherein the C6-C18 aryl groups are independently unsubstituted or substituted with at least one second group; the second group is one or more of deuterium, nitro, halogen, cyano and carbonyl.
4. The phosphorescent iridium complex according to claim 1, wherein the C4-C12 aromatic heterocyclic group is an unsubstituted or substituted aromatic heterocyclic group with at least one third group; the third group is one or more of deuterium, halogen, cyano and nitro.
5. The phosphorescent iridium complex of claim 1 wherein the halogen is fluorine.
6. The phosphorescent iridium complex of claim 1, wherein the chemical structural formula of the phosphorescent iridium complex is one of formula L-001 to formula L-108:
Figure FDA0002451521300000021
Figure FDA0002451521300000031
Figure FDA0002451521300000041
Figure FDA0002451521300000051
Figure FDA0002451521300000061
Figure FDA0002451521300000071
7. a method for preparing a phosphorescent iridium complex according to any one of claims 1 to 6, comprising the steps of:
reacting a reactant A with a general formula A with iridium trichloride to obtain a bridged ligand B;
reacting the bridging ligand B with a diketone derivative with a general formula of C to obtain the phosphorescent iridium complex;
Figure FDA0002451521300000072
8. the method for preparing a phosphorescent iridium complex according to claim 7, wherein the step of reacting a reactant A with a general formula A and iridium trichloride to obtain a bridged ligand B specifically comprises:
mixing a reactant A with a general formula of A, iridium trichloride, ethylene glycol ethyl ether and water, and then placing the mixture in a protective atmosphere for reaction to obtain a bridged ligand B.
9. The method according to claim 7, wherein the step of reacting the bridged ligand B with a diketone derivative having a general formula C to obtain the phosphorescent iridium complex comprises:
and mixing the bridging ligand B, potassium carbonate and ethylene glycol ethyl ether, placing the mixture in a protective atmosphere at the temperature of 110-120 ℃, and adding a diketone derivative with the general formula of C for reaction to obtain the phosphorescent iridium complex.
10. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, wherein the organic layer partially or entirely comprises the phosphorescent iridium complex as claimed in any one of claims 1 to 6.
CN202010294091.XA 2020-04-15 2020-04-15 Phosphorescent iridium complex, preparation method thereof and organic electroluminescent device Pending CN111303213A (en)

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CN111690017A (en) * 2020-07-15 2020-09-22 奥来德(上海)光电材料科技有限公司 Organic electroluminescent material and preparation method and application thereof
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