CN111233935B - Iridium complex, preparation method and organic electroluminescent device comprising iridium complex - Google Patents
Iridium complex, preparation method and organic electroluminescent device comprising iridium complex Download PDFInfo
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- 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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Abstract
The invention discloses a metal iridium complex, a preparation method and application thereof. By adjusting the wavelength of the compound, the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency and the service life of the device are improved. The preparation method of the iridium complex provided by the invention has the characteristics of simple synthesis steps, low requirement on conditions and high yield of target products, and is suitable for popularization and application.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a metal iridium complex, a preparation method and an organic electroluminescent device containing the same.
Background
Currently, in 1987, deng Qingyun doctor reported that electroluminescent diode technology based on organic luminescent materials mainly adopts vacuum evaporation to prepare a double-layer device with a transmission layer and a luminescent layer, the quantum efficiency is improved to 1%, and the quantum efficiency can reach 1000cd/m under the working voltage of less than 10V 2 The brightness of the organic electroluminescent device is widely paid attention to by world science lovers, and the organic electroluminescent technology is pushed to the step of practical application. The electroluminescent device has an all-solid-state structure, and the organic electroluminescent material is the core and the foundation of the device. The development of new materials is a source of driving the continuous progress of electroluminescent technology. The preparation of the original materials and the optimization of devices are also research hot spots of the current organic electroluminescent industry.
Since the phosphorescence has been found, the luminous efficiency of the phosphorescent material is significantly higher than that of fluorescence, and can reach 100% in theory, so many scientific research institutions are increasing the research and development efforts of the phosphorescent material, and attempt to accelerate the industrialized development of the phosphorescent material. However, the phosphorescent materials have high synthesis price, high synthesis process requirements, easy environmental pollution in the synthesis process, high purification requirements and low efficiency.
Therefore, research on an organic phosphorus luminescent material with high luminous efficiency and good purification effect is a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the above, the invention provides a metallic iridium complex, a preparation method and application thereof, and an organic electroluminescent device containing the compound. According to the novel material provided by the invention, the specific ligand is selected, so that the obtained organic metal compound is used for an organic electroluminescent device, and the luminous efficiency and the service life of the device are improved.
In order to achieve the above purpose, the present invention adopts the following technical scheme: the metallic iridium complex is characterized by having a molecular structural general formula as follows:
wherein m is 0, 1 or 2, n is 1, 2 or 3, m+n=3;
R 1 、R 2 、R 3 、R 4 and R is 5 Are all any one of hydrogen, deuterium, nitro, amino, hydroxyl, halogen, cyano, mercapto, C1-C8 alkyl, C1-C8 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C6-C18 aryl and C4-C12 aromatic heterocyclic.
Preferably, said R 1 、R 2 And R is 5 The number of substituents is 0, 1, 2, 3 or 4, R 3 And R is 4 The number of substituents is 0, 1 or 2.
Preferably, the C1-C8 alkyl is a linear, branched or cyclic alkyl group which is unsubstituted or substituted with at least 1 substituent I; the C6-C18 aryl is unsubstituted or aryl substituted with at least 1 substituent I;
wherein the substituent I is at least one of deuterium, nitro, amino, hydroxyl, halogen, cyano, carbonyl and sulfhydryl.
Preferably, the C4-C12 aromatic heterocyclic group is an unsubstituted or at least 1 substituent II-substituted aromatic heterocyclic group;
wherein the heteroatom in the aromatic heterocyclic group is nitrogen, sulfur or oxygen; the substituent II is halogen, deuterium, amino, cyano, nitro, hydroxyl or sulfhydryl.
Preferably, said R 1 、R 2 、R 3 、R 4 、R 5 Forms any one of a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C6-C60 condensed ring and a substituted or unsubstituted C5-C60 spiro ring with the ring of each ring.
Preferably, said R 1 And R is R 2 Between R and R 3 、R 4 And R is R 5 Any adjacent substituents form any one of a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocyclic ring, a C6-C60 condensed ring and a substituted or unsubstituted C5-C60 spiro ring.
Preferably, the substituent for substitution is any one of hydrogen, deuterium, halogen, cyano, C1-C12 alkyl, C6-C18 aryl, C4-C12 aromatic heterocyclic group, C8-C16 condensed ring group, C5-C60 spiro ring.
The following is a preferred structure of the iridium metal complex I:
the invention also provides a preparation method of the iridium complex, which comprises the following steps:
(1) Under the protection of nitrogen, fully reacting the compound A with iridium trichloride to obtain a compound B;
(2) Fully reacting the compound B obtained in the step (1) with silver trifluoromethane sulfonate to obtain a compound C;
(3) Fully reacting the compound C obtained in the step (2) with the compound D to obtain a compound I;
the structural formula of the compound A is as follows:
the structural formula of the compound B is as follows:
the structural formula of the compound C is as follows:
the structural formula of the compound D is as follows:
preferably, the preparation method of the iridium metal complex comprises the following steps: when m=2 and n=1 in the compound i, the synthetic route is as follows:
when m=1 and n=2 in the compound i, the synthetic route is as follows:
when m=0 and n=3 in the compound i, the synthetic route is as follows:
the preparation method of the iridium complex provided by the invention has the characteristics of simple synthesis steps, low requirement on conditions, high yield of target products and the like.
Preferably, the molar mass ratio of the compound a to iridium trichloride in the step (1) is 62 to 75: 24-25; the molar mass ratio of the compound B to the silver trifluoromethane sulfonate in the step (2) is 4-5: 9-20; the molar mass ratio of the compound C to the compound D in the step (3) is 8-9: 16-34.
Preferably, in the step (1), the mass ratio of the volume of the added solvent to the iridium trichloride is 300-400mL:8-10g, wherein the solvent is a mixed solution of glycol diethyl ether and water, and the volume ratio of the glycol diethyl ether to the water is 3:1.
Preferably, in the step (2), the volume ratio of the added methanol to the dichloromethane is 5:2; the mass ratio of the volume of the mixed solution of methanol and methylene dichloride to the silver triflate is 40-66mL:3-4g.
The invention also provides application of the iridium complex in preparation of the organic electroluminescent device.
An organic electroluminescent device comprising: the organic compound comprises a first electrode, a second electrode and an organic compound layer arranged between the two electrodes, wherein the organic compound layer comprises the metal iridium complex.
Preferably, the organic layer comprises one or more of a hole injection layer, a hole transport layer, a layer with hole injection and hole transport skills, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer with electron transport and electron injection skills, and at least one layer comprises the iridium complex.
Preferably, the organic layer includes a light emitting layer including a host material and the iridium complex.
Preferably, in the above scheme, the mass ratio of the host material to the iridium metal complex is 90:10-99.5:0.5.
The organic electroluminescent device in the invention can be used for organic luminescent devices, organic solar cells, electronic papers, organic photoreceptors or organic thin film transistors.
Compared with the prior art, the invention has the following beneficial effects: the metal iridium complex with the novel structure provided by the invention is combined with the ligand of the specific heterocycle to adjust the wavelength of the compound, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved.
Detailed Description
The technical solutions of the embodiments of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
A process for the preparation of the compound numbered L001:
(1) Under a nitrogen protection system, A-001 (64.5 mmol,10 g) and IrC1 were weighed 3 ·3H 2 O (24.8 mmo1,8.75 g) was put into a reaction system, 300mL of a mixed solution of ethylene glycol ether and 100mL of purified water was added, refluxed for 24 hours under the protection of nitrogen, then cooled to 25℃and precipitates were precipitated, the precipitates were suction-filtered, and washed and dried with water, absolute ethanol and petroleum ether in this order (80℃for 8 hours), to give a yellow powder of the bridged ligand B-001 (6.64 g, yield: 50%).
(2) Intermediate B-001 (4.67 mmol,5 g) was weighed, silver trifluoromethane sulfonate (14 mmol,3.6 g) was added, 100mL of dichloromethane was further added to the system, 40mL of methanol was added, reflux was performed for 24 hours under nitrogen protection, cooling was performed to 25 ℃, and the column chromatography (short column) filtrate was concentrated until solid precipitation, to obtain iridium complex intermediate C-001 (6.18 g, yield 93%) as a yellowish green powder.
(3) Intermediate C-001 (8.4 mmol,5.97 g) was weighed, ligand D-001 (25.5 mmol,7 g) was added, and then 120mL of absolute ethanol was added to the system, refluxed for 24 hours under nitrogen protection, suction filtration, alcohol washing, drying (80 ℃ C., 8 h) was performed, dichloromethane was used as a solvent, silica gel column chromatography was used, and the filtrate was concentrated until solid was precipitated, to obtain final yellow compound L001 (2.02 g, yield 31%). The process flow is as follows:
HPLC purity is greater than 99%.
Mass spectrum calculated as 775.89; the test value was 776.73.
Elemental analysis:
the calculated values are: 60.37 percent of C; h3.51%; n is 7.22%; 4.12% of O; 24.77% of Ir;
the test values are: 60.38 percent of C; h3.52%; 7.21% of N; 4.11% of O; 24.76% of Ir.
Example 2
A process for the preparation of compound No. L009:
(1) Under a nitrogen protection system, weighing A-009 (64.5 mmol,10 g), putting IrC 13.3H2O (24.8 mmo1,8.75 g) into a reaction system, adding 300mL of a mixed solution of ethylene glycol diethyl ether and 100mL of purified water, refluxing for 24 hours under nitrogen protection, cooling to 25 ℃, precipitating, filtering the precipitate, washing and drying the precipitate with water, absolute ethyl alcohol and petroleum ether in sequence (80 ℃ C., 8H), and obtaining a yellow powder of bridged ligand B-009 (6.64 g, yield 50%).
(2) Intermediate B-009 (4.67 mmol,5 g) was weighed out, silver triflate (14 mmol,3.6 g) was added, 100mL of dichloromethane was added to the system, 40mL of methanol was added, the mixture was refluxed for 24 hours under nitrogen protection, cooled to 25 ℃, and the column chromatography (short column) filtrate was concentrated until a solid precipitated, to give iridium complex intermediate C-009 (8.16 g, 93% yield) as a yellowish green powder.
(3) Intermediate C-009 (8.4 mmol,5.97 g) was weighed, ligand D-009 (25.5 mmol,8.47 g) was added, and then 120mL of absolute ethyl alcohol was added to the system, and under nitrogen protection, the mixture was refluxed for 24 hours, filtered, washed with alcohol, dried (80 ℃ C., 8 h), and chromatographed on a silica gel column using methylene chloride as solvent, the filtrate was concentrated to solid precipitate, thus obtaining the final yellow compound L009 (2.16 g, 31% yield). The process flow is as follows:
HPLC purity is greater than 99%.
Mass spectrum calculated as 832.00; the test value was 833.26.
Elemental analysis:
calculated C62.08%; h4.24%; 6.73 percent of N; 3.85% of O; 23.10 percent of Ir;
the test value is 62.07 percent of C; h4.23%; 6.74% of N; 3.86% of O; 23.11% of Ir.
Example 3
A process for the preparation of the compound numbered L021:
step 1, weighing A-021 (64.5 mmol,10.91 g) under a nitrogen protection system, putting IrC 13.3H2O (24.8 mmo1,8.75 g) into the reaction system, adding 300mL of a mixed solution of ethylene glycol diethyl ether and 100mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to 25 ℃, precipitating, filtering the precipitate, washing and drying the precipitate with water, absolute ethyl alcohol and petroleum ether in sequence (80 ℃ for 8H), and obtaining yellow powder of bridging ligand B-021 (7.27 g, yield is 52%).
Step 2, intermediate B-021 (4.67 mmol,5.26 g) was weighed, silver trifluoromethane sulfonate (14 mmol,3.6 g) was added, 100mL of dichloromethane was further added to the system, 40mL of methanol was added under nitrogen protection, reflux was performed for 24 hours, cooling to 25 ℃, and column chromatography (short column) filtrate was concentrated to solid precipitation to obtain iridium complex intermediate C-021 (6.35 g, yield 92%) as a yellowish green powder.
Step 3, intermediate C-021 (8.4 mmol,6.21 g) was weighed, ligand D-021 (25.5 mmol,7.4 g) was added, then 120mL of absolute ethyl alcohol was added to the system, the mixture was refluxed for 24 hours under the protection of nitrogen, suction filtration, alcohol washing, drying (80 ℃ C., 8 h) was performed, dichloromethane was used as a solvent, silica gel column chromatography was performed, and the filtrate was concentrated to solid precipitation, to obtain final yellow compound L021 (2.06 g yield 30%). The process flow is as follows:
HPLC purity is greater than 99%.
Mass spectrum calculated as 817.97; the test value was 818.72.
Elemental analysis:
calculated C61.67%; h4.07%; 6.85% of N; 3.91% of O; 23.50% of Ir; the test value is C61.66%; h4.06%; 6.86% of N; 3.92% of O; 23.51% of Ir.
Example 4
A process for the preparation of the compound numbered L091:
step 1, weighing A-091 (64.5 mmol,17.82 g) under a nitrogen protection system, putting IrC 13.3H2O (24.8 mmo1,8.75 g) into a reaction system, adding 300mL of a mixed solution of ethylene glycol diethyl ether and 100mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to 25 ℃, precipitating, filtering the precipitate, washing and drying the precipitate with water, absolute ethyl alcohol and petroleum ether in sequence (80 ℃ for 8H), and obtaining the yellow powder of bridging ligand B-091 (10.22 g, yield is 53%).
Step 2, intermediate B-091 (4.67 mmol,7.26 g) was weighed, silver trifluoromethane sulfonate (14 mmol,3.6 g) was added, 100mL of dichloromethane was further added to the system, 40mL of methanol was added, under nitrogen protection, reflux was performed for 24 hours, cooling to 25 ℃, and column chromatography (short column) filtrate was concentrated to solid precipitation to obtain iridium complex intermediate C-091 (8.19 g, 92% yield) as a yellowish green powder.
Step 3, intermediate C-091 (8.4 mmol,8.01 g) was weighed, ligand D-091 (25.5 mmol,3.95 g) was added, and then 120mL of absolute ethyl alcohol was added to the system, and under the protection of nitrogen, the mixture was refluxed for 24 hours, suction filtration, alcohol washing, drying (80 ℃ C., 8 h) was performed, dichloromethane was used as a solvent, silica gel column chromatography was performed, and the filtrate was concentrated to precipitate a solid, thereby obtaining final yellow compound L091 (2.48 g, yield 33%).
The process flow is as follows:
HPLC purity is greater than 99%.
Mass spectrum calculated as 896.98; the test value was 897.45.
Elemental analysis:
calculated C60.26%; h3.37%; n is 7.81%; 7.13% of O; 21.43% Ir;
the test value is C60.25%; h3.38%; n is 7.81%; 7.12% of O; ir 21.43%.
Example 5
A process for the preparation of the compound numbered L104:
step 1, weighing A-104 (64.5 mmol,19.8 g) under a nitrogen protection system, putting IrC 13.3H2O (24.8 mmo1,8.75 g) into a reaction system, adding 300mL of a mixed solution of ethylene glycol diethyl ether and 100mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to 25 ℃, precipitating, filtering the precipitate, washing and drying the precipitate with water, absolute ethyl alcohol and petroleum ether in sequence (80 ℃ for 8H), and obtaining the bridged ligand B-104 (11.25 g, yield is 54%) of yellow powder.
Step 2, intermediate B-104 (4.67 mmol,7.84 g) was weighed, silver trifluoromethane sulfonate (14 mmol,3.6 g) was added, 100mL of dichloromethane was further added to the system, 40mL of methanol was added, the mixture was refluxed for 24 hours under nitrogen protection, cooled to 25 ℃, and the column chromatography (short column) filtrate was concentrated until solid was precipitated, to obtain iridium complex intermediate C-104 (8.73 g, 92% yield) as a yellowish green powder.
Step 3, intermediate C-104 (8.4 mmol,8.53 g) was weighed, ligand D-104 (25.5 mmol,3.95 g) was added, then 120mL of absolute ethyl alcohol was added to the system, the mixture was refluxed for 24 hours under the protection of nitrogen, the mixture was filtered by suction, washed with alcohol, dried (80 ℃ for 8 hours), and subjected to silica gel column chromatography using methylene chloride as a solvent, and the filtrate was concentrated to precipitate a solid, thereby obtaining final yellow compound L104 (2.49 g, yield 31%). The process flow is as follows:
HPLC purity is greater than 99%.
Mass spectrum calculated as 959.13; the test value was 960.08.
Elemental analysis:
the calculated values are: 61.36 percent of C; h4.62%; 7.30% of N; 6.67% of O; 20.04% of Ir;
the test values are: 61.35 percent of C; h4.63%; 7.31% of N; 6.68% of O; 20.03% of Ir.
Example 6
A process for the preparation of the compound numbered L126:
step 1, under a nitrogen protection system, weighing A-129 (64.5 mmol,17.82 g), putting IrC 13.3H2O (24.8 mmo1,8.75 g) into a reaction system, adding 300mL of a mixed solution of ethylene glycol diethyl ether and 100mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to 25 ℃, precipitating, filtering the precipitate, washing and drying the precipitate with water, absolute ethyl alcohol and petroleum ether in sequence (80 ℃ for 8H), and obtaining the bridged ligand B-126 (10.22 g, yield is 53%) of yellow powder.
Step 2, intermediate B-126 (4.67 mmol,7.26 g) was weighed, silver trifluoromethane sulfonate (14 mmol,3.6 g) was added, 100mL of dichloromethane was further added to the system, 40mL of methanol was added, the mixture was refluxed for 24 hours under nitrogen protection, cooled to 25 ℃, and the column chromatography (short column) filtrate was concentrated until solid was precipitated to obtain iridium complex intermediate C-126 (8.19 g, 92% yield) as a yellowish green powder.
Step 3, intermediate C-126 (8.4 mmol,8.01 g) was weighed, ligand D-126 (25.5 mmol,7.04 g) was added, then 120mL of absolute ethyl alcohol was added to the system, the mixture was refluxed for 24 hours under the protection of nitrogen, the mixture was filtered by suction, washed with alcohol, dried (80 ℃ C., 8 h), and subjected to silica gel column chromatography using methylene chloride as a solvent, and the filtrate was concentrated to precipitate a solid, thereby obtaining final yellow compound L126 (2.82 g, yield 33%). The process flow is as follows:
HPLC purity is greater than 99%.
Mass spectrum calculated as 1018.08; the test value was 1019.15.
Elemental analysis:
the calculated values are: c, 60.17%; h3.27%; 8.25% of N; 9.43% of O; 18.88% of Ir; the test values are: 60.16 percent of C; h3.28%; n is 8.24%; 9.44% of O; 18.87% of Ir.
Example 7
The preparation method of formula L003 was the same as that of example 1;
mass spectrum theory: 789.92; mass spectrometry test values: 790.54.
example 8
The preparation method of formula L004 is the same as that of example 1;
mass spectrum theory: 817.97; mass spectrometry test values: 818.23.
example 9
The preparation method of formula L008 is the same as that of example 1;
mass spectrum theory: 789.92; mass spectrometry test values: 790.42.
example 10
The preparation method of formula L017 is the same as that of example 1;
mass spectrum theory: 803.94; mass spectrometry test values: 804.61.
example 11
The preparation method of formula L020 is the same as that of example 1;
mass spectrum theory: 817.97; mass spectrometry test values: 818.65.
example 12
The preparation method of formula L023 is the same as that of example 1;
mass spectrum theory: 820.99; mass spectrometry test values: 821.87.
example 13
The preparation method of formula L051 is the same as that of example 1;
mass spectrum theory: 835.01; mass spectrometry test values: 836.12.
example 14
The preparation method of formula L066 is the same as that of example 1;
mass spectrum theory: 852.06; mass spectrometry test values: 853.41.
example 15
The preparation method of formula L070 is the same as that of example 1;
mass spectrum theory: 866.09; mass spectrometry test values: 867.32.
example 16
The preparation method of formula L112 is the same as that of example 2;
mass spectrum theory: 1023.23; mass spectrometry test values: 1024.32.
example 17
An organic electroluminescent device was prepared using the organic phosphorus luminescent material (iridium metal complex) of formula L001 in example 1, and the specific process was as follows:
the thickness of the coating is equal to
The ITO glass substrate is washed for 2 times in distilled water for 30 minutes by ultrasonic wave, repeatedly washed for 2 times by distilled water for 10 minutes by ultrasonic wave, and after the distilled water is washed, solvents such as methanol, acetone, isopropanol and the like are washed by ultrasonic wave in sequence, dried and transferred into a plasma washer, and the substrate is washed for 5 minutes and then is sent into a vapor deposition machine.
The ITO is used as an anode, N1- (2-naphthyl) -N4, N4-bis (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine ("2-TNATA") is firstly evaporated at 60nm, NPB 60nm, a main substance 4,4'-N, N' -biphenyl dicarbazole ("CBP") and a doping substance compound formula L00190 are then evaporated at 10 weight ratio, the mixed evaporation is performed at 30nm, the evaporation hole blocking layer ("BAlq") is at 10nm, the evaporation electron transport layer "Alq3" is at 40nm, the evaporation electron injection layer LiF0.2nm and the evaporation cathode Al is at 150 nm. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 18
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L009 prepared in example 2. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 19
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L021 prepared in example 3. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 20
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L091 prepared in example 4. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 21
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L104 prepared in example 5. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 22
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L126 prepared in example 6. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 23
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L003 prepared in example 7. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 24
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L004 prepared in example 8. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 25
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L008 prepared in example 9. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 26
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L017 prepared in example 10. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 27
An organic electroluminescent device was prepared in the same manner as in example 17 using the formula L020 prepared in example 11. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 28
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L023 prepared in example 12. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 29
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L051 prepared in example 13. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 30
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L066 prepared in example 14. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 31
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L070 prepared in example 15. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Example 32
An organic electroluminescent device was prepared in the same manner as in example 17 using formula L112 prepared in example 16. And testing the performance luminescence characteristics of the obtained device, and measuring by using a KEITHLEY 2400 source measuring unit and a CS-2000 spectroradiometer to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
Comparative example 1
An organic electroluminescent device was prepared in the same manner as in example 17, and the green light-emitting layer doped compound had the following structure:
the same examination as in examples 17 to 32 was carried out on the organic electroluminescent devices thus prepared, and the results are shown in Table 1.
TABLE 1 detection results of organic electroluminescent devices in examples 17 to 32 and comparative example 1
As can be seen from table 1, compared with the organic electroluminescent device prepared by using the comparative compound Ir (ppy) 3 as the light-emitting layer doping material, the organic electroluminescent device prepared by using the organic phosphorus light-emitting material as the light-emitting layer doping material provided by the present invention has significantly reduced driving voltage, significantly improved light-emitting efficiency and significantly improved lifetime.
In the present specification, each embodiment is described in a progressive manner, and each embodiment is mainly described in a different point from other embodiments, and identical and similar parts between the embodiments are all enough to refer to each other. For the device disclosed in the embodiment, since it corresponds to the method disclosed in the embodiment, the description is relatively simple, and the relevant points refer to the description of the method section.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (2)
1. A metallic iridium complex, characterized in that the molecular structural formula of the metallic iridium complex is selected from any one of the following structures:
2. use of the iridium metal complex as claimed in claim 1 in organic electroluminescent devices.
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| CN110862418A (en) * | 2019-11-29 | 2020-03-06 | 吉林奥来德光电材料股份有限公司 | Iridium metal complex and preparation method and application thereof |
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