CN112778373A - Iridium metal complex, preparation method thereof and organic electroluminescent device - Google Patents
Iridium metal complex, preparation method thereof and organic electroluminescent device Download PDFInfo
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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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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Abstract
The invention discloses an iridium metal complex, a preparation method thereof and an organic electroluminescent device, wherein the iridium metal complex has the following structural formula:
Description
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to an iridium metal complex, a preparation method thereof and an organic electroluminescent device.
Background
The organic electroluminescence technology is a latest generation flat panel display technology, and can be used for flat panel displays and illumination light sources, and currently, commercial flat panel displays are put into the market, and the illumination light sources are rapidly industrialized due to their own absolute advantages. The electroluminescent device has an all-solid-state structure, organic electroluminescent materials are the core and the foundation of the device, and the development of new materials is the source power for promoting the continuous progress of the electroluminescent technology. The preparation of the original material and the optimization of the device are also the research hotspots of the organic electroluminescent industry at present.
The phosphorescence luminescent phenomenon is always favored since the discovery, because the luminescent efficiency of the phosphorescence material is obviously higher than the luminescent efficiency of the fluorescence, theoretically reaching 100 percent of the luminescent efficiency, many scientific research institutions are increasing the research and development of the phosphorescence material and trying to accelerate the industrialized development through the phosphorescence material; however, the phosphor material has high synthesis cost, high synthesis process requirements, high purification requirements and low efficiency, and easily pollutes the environment in the synthesis process.
Disclosure of Invention
An object of the present invention is to provide an iridium metal complex, a method for preparing the same, and an organic electroluminescent device, which solve the problems set forth in the background art.
In order to achieve the purpose, the invention provides the following technical scheme:
an iridium metal complex having a structural formula shown in chemical formula 1:
R1、R2、R3、R4、R5and R6Each independentlySelected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, or substituted or unsubstituted C8-C16 condensed ring group, R4、R5Is an alkane, R6Is hydrogen;
R1、R2、R3the substitution position is any position of the ring; r1The number of the substituents is 0-3, R2The number of substituents is 0-4, R3The number of the substituents is 0 to 4.
As a further scheme of the invention: the alkyl is straight-chain alkyl, branched-chain alkyl, cycloalkyl, straight-chain alkyl substituted by at least 1 substituent, branched-chain alkyl substituted by at least 1 substituent or cycloalkyl substituted by at least 1 substituent; wherein, the substituent is one or more of halogen, deuterium, cyano, hydroxyl and sulfydryl independently.
As a still further scheme of the invention: the aryl group is preferably an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy or mercapto.
As a still further scheme of the invention: the aromatic heterocyclic group is preferably an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxyl or mercapto.
As a still further scheme of the invention: r1、R2、R3Independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle, a substituted or unsubstituted C6-C60 fused ring or a substituted or unsubstituted C5-C60 spiro ring with other substituents on the ring;
or R1、R2、R3Form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C60 aromatic ring, a substituted or unsubstituted C2-C60 aromatic heterocycle, a substituted or unsubstitutedA C6-C60 fused ring, or substituted or unsubstituted C5-C60 spiro ring;
the substituent on the substituent group is at least one selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, substituted or unsubstituted C8-C16 condensed ring group and substituted or unsubstituted C5-C60 spiral ring.
As a still further scheme of the invention: in the above technical solution, it is most preferable that the iridium metal complex is selected from any one of the following structures:
some specific structural forms are listed above, but the series of compounds are not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of the groups and the substituted groups and substituted positions thereof, which is not described in detail herein.
The preparation method of the iridium metal complex comprises the following steps:
1) providing compound a and compound C, respectively, represented by the following structural formulae:
2) fully reacting the raw material A with iridium trichloride to prepare a bridging ligand intermediate B;
3) and fully reacting the intermediate B with the intermediate C to obtain the iridium metal complex shown in the chemical formula 1.
As a still further scheme of the invention: the structure of bridging ligand intermediate B is:
the synthetic route is as follows:
An organic electroluminescent device comprises the iridium metal complex, a first electrode, a second electrode and an organic layer arranged between the first electrode and the second electrode, wherein the organic layer comprises the iridium metal complex shown in chemical formula 1; the iridium metal complex shown in chemical formula 1 of the present invention may be present in the organic material layer in a single form or mixed with other materials;
the organic layer at least comprises one or more of a hole injection layer, a hole transport layer, a layer with hole injection and hole transport functions, an electron blocking layer, a luminescent layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer with electron transport and electron injection functions
As a still further scheme of the invention: the organic electroluminescent device comprises at least one functional layer containing an iridium metal complex represented by chemical formula 1 of the present invention.
The organic electroluminescent device includes a light emitting layer containing an iridium metal complex represented by chemical formula 1 of the present invention. Preferably, the light emitting layer of the organic electroluminescent device includes a host material and a dopant material, and the dopant material is an iridium metal complex represented by chemical formula 1 of the present invention. Further preferably, the mixing ratio of the host material and the doping material of the luminescent layer is 90:10-99.5:0.5, and the device can be used for an organic luminescent device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
Compared with the prior art, the invention has the beneficial effects that: the iridium metal complex with the novel structure provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency and the brightness of the device are improved. The preparation method of the iridium metal complex provided by the invention is simple in preparation steps and high in product purity.
Detailed Description
The technical solutions of the present invention will be described in further detail with reference to specific embodiments, and it should be apparent that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
An iridium metal complex L001, namely a compound with the number of 001, comprises the following specific synthetic steps:
1) weighing A-001(69.4mmol, 20g IrCl) under nitrogen protection system3·3H2Placing O23.1mmo1 (8.1 g) into a reaction system, adding a mixed solution of 600mL of ethylene glycol ethyl ether and 200mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, performing suction filtration on the precipitate, and sequentially washing and drying with water, absolute ethyl alcohol and petroleum ether to obtain a red-powder bridged ligand B-001(9.2g, the yield is 50%);
2) weighing intermediate B-0015.75mmol (namely 9.2g), adding ligand 3, 7-diethyl-4, 6-nonanedione C-001(3.4g), adding 200mL of ethylene glycol ethyl ether and potassium carbonate (8g) into the system, stirring for 24 hours at 120 ℃ under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating the filtrate to separate out a solid to obtain a final red compound L001(3.4g, yield 30%);
HPLC purity is more than 99.5 percent;
mass spectrum calculated 978.31; test value 978.30;
elemental analysis, calculated value C is 65.07 percent; 6.29 percent of H; 5.73 percent of N; 3.27 percent of O; 19.65 percent of Ir; the test value is 65.05 percent of C; 6.30 percent of H; 5.70 percent of N; 3.30 percent of O; 19.66 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 2
An iridium metal complex L005, namely a compound with the number of 005, comprises the following specific synthetic steps:
1) weighing A-005(66mmol, 20g) and IrCl under nitrogen protection system3·3H2Placing O22mmo1 (namely 7.8g) into a reaction system, adding a mixed solution of 600mL of ethylene glycol ethyl ether and 200mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, carrying out suction filtration on the precipitate, washing with water, absolute ethyl alcohol and petroleum ether in sequence, and drying to obtain a red-powder bridged ligand B-005(10.8g, the yield is 60%);
2) weighing intermediate B-0056mmol (namely 10g), adding ligand 3, 7-diethyl-4, 6-nonanedione C-005(3.6g), adding 200mL of ethylene glycol ethyl ether and potassium carbonate (8.3g) into the system, stirring for 24 hours at 120 ℃ under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating and separating out solid from filtrate to obtain a final red compound L005(3g, yield 40%);
HPLC purity is more than 99.5 percent;
mass spectrum calculated 1006.37; test value 1006.35;
elemental analysis calculated C: 65.64%; 6.51 percent of H; 5.57 percent of N; 3.18 percent of O; 19.10 percent of Ir; the test value is 65.62 percent of C; 6.50 percent of H; 5.60 percent of N; 3.20 percent of O; 19.10 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 3
An iridium metal complex L019, namely a compound with the number of 019, comprises the following specific synthetic steps:
1) a-019(69.4mmol, 20g of IrCl) was weighed under a nitrogen protection system3·3H2Placing O23.1mmo1 (8.1 g) into a reaction system, adding a mixed solution of 600mL of ethylene glycol ethyl ether and 200mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, performing suction filtration on the precipitate, and sequentially washing and drying with water, absolute ethyl alcohol and petroleum ether to obtain a red-powder bridged ligand B-019(9.2g, the yield is 50%);
2) weighing intermediate B-0195.75mmol (9.2 g), adding ligand acetylacetone C-01917.25mmol (1.7g), adding ethylene glycol ethyl ether 200mL and potassium carbonate (8g) into the system, stirring at 120 ℃ for 24 hours under the protection of nitrogen, performing suction filtration, performing alcohol washing, performing petroleum ether washing, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating the filtrate to separate out solid, thereby obtaining a final red compound L019(3.5g, yield 35%);
HPLC purity is more than 99.5 percent;
mass spectrum calculated 866.10; test value 866.20;
elemental analysis, calculated value C is 62.41 percent; 5.24 percent of H; 6.47 percent of N; 3.69 percent of O; 22.19 percent of Ir; the test value is C: 62.40%; 5.25 percent of H; 6.50 percent of N; 3.70 percent of O; 22.20 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 4
An iridium metal complex L043, namely a compound with the number of 043, comprises the following specific synthetic steps:
1) weighing A-043(73.0mmol, 20g IrCl) under nitrogen protection system3·3H2Adding O24.3mmo1 (8.6 g) into reaction system, adding mixed solution of 600mL of ethylene glycol ethyl ether and 200mL of purified water, refluxing for 24 hr under nitrogen protection, cooling to room temperature, precipitating, filtering, adding water and anhydrousWashing and drying the mixture by ethanol and petroleum ether in turn to obtain a red powdered bridging ligand B-043(9.8g, the yield is 52%);
2) weighing intermediate B-0435.8mmol (9 g), adding ligand C-04317.4mmol (2.7g), adding 180mL of ethylene glycol ethyl ether and potassium carbonate (8g) into the system, stirring at 120 ℃ for 24 hours under the protection of nitrogen, performing suction filtration, washing with alcohol, washing with petroleum ether, drying, using dichloromethane as a solvent, performing silica gel column chromatography, and concentrating the filtrate to separate out solid to obtain a final red compound L043(4.1g, the yield is 39.5%);
HPLC purity is more than 99 percent;
mass spectrum calculated 894.15; test value 894.20;
elemental analysis calculated C: 63.13%; 5.52 percent of H; 6.27 percent of N; 3.58 percent of O; 21.50 percent of Ir; the test value is C: 63.10%; 5.50 percent of H; 6.30 percent of N; 3.60 percent of O; 21.50 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
Example 5
An iridium metal complex L059, namely a compound with the number 059, comprises the following specific synthetic steps:
1) weighing A-059(66mmol, 20g) and IrCl under the protection of nitrogen3·3H2Placing O22mmo1 (namely 7.8g) into a reaction system, adding a mixed solution of 600mL of ethylene glycol ethyl ether and 200mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, carrying out suction filtration on the precipitate, washing with water, absolute ethyl alcohol and petroleum ether in sequence, and drying to obtain a red-powder bridged ligand B-059(10.8g, the yield is 60%);
2) weighing intermediate B-0596mmol (namely 10g), adding ligand C-05918mmol (2.8g), adding ethylene glycol ethyl ether 200mL and potassium carbonate (8g) into the system, stirring at 120 ℃ for 24 hours under the protection of nitrogen, carrying out suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, carrying out silica gel column chromatography, concentrating the filtrate to obtain a solid, and separating out the solid to obtain a final red compound L059(3.5g, yield 31%);
HPLC purity greater than 99.5%;
mass spectrum calculated 984.40; test value 984.50;
elemental analysis, calculated value C is 64.46 percent; 6.05 percent of H; 5.90 percent of N; 3.37 percent of O; 20.23 percent of Ir; the test value is C: 64.50%; 6.10 percent of H; 5.93 percent of N; 3.40 percent of O; 20.20 percent of Ir.
Specifically, the reaction formulae of steps 1) to 2) are as follows:
in the embodiment, the iridium metal complex is applied to preparation of organic electroluminescent device products.
The present invention also provides an organic electroluminescent device made of the iridium metal complex, more particularly, the iridium metal complex represented by chemical formula 1.
Example 6
An organic electroluminescent device was prepared using the compound L001 prepared in example 1, which is more specifically:
coating with a thickness of
The ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. Firstly, the upper surface of ITO (anode) is evaporated with CuPc
Followed by deposition of NPB
Host substance 4, 4'-N, N' -biphenyl dicarbazole ('CBP') and doping substance compound L00195: 5 in weight ratio are mixed for evaporation
Vapor-deposited electron transport layer "Alq3"
Depositing an electron injection layer LiF
And vapor deposition of cathode Al
And (4) preparing the organic electroluminescent device. And testing the performance luminescence characteristics of the obtained device, wherein a KEITHLEY2400 type source measuring unit and a CS-2000 spectral radiance luminance meter are adopted for measurement so as to evaluate the driving voltage, the current efficiency and the power efficiency.
Referring to the above method, the compound L001 was replaced with L005, L019, L043, and L059, respectively, to prepare an organic electroluminescent device of the corresponding compound.
Comparative example 1
An organic electroluminescent device was prepared in the same manner as in example 6, and the structure of the light-emitting layer-doped compound was as follows:
the same examination as in example 6 was performed on the prepared organic electroluminescent device, and the results are shown in table 1.
Table 1 test results of organic electroluminescent devices in example 6 and comparative example 1
Table 1 it can be seen that the present invention is usedOrganic electroluminescent device prepared by using iridium metal complex as luminescent layer doping material and using comparison compound Ir (pq)2Compared with an organic electroluminescent device prepared by using acac as a luminescent layer doping material, the organic electroluminescent device has the advantages that the driving voltage is obviously reduced, and the current efficiency and the power efficiency are obviously improved.
The invention has the beneficial effects that: the iridium metal complex with the novel structure provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved. The preparation method of the iridium metal complex provided by the invention is simple in preparation steps and high in product purity.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (8)
1. An iridium metal complex having a structural formula shown in chemical formula 1:
R1、R2、R3、R4、R5and R6Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C4-C12 aromatic heterocyclic group, or substituted or unsubstituted C8-C16 condensed ring group, R4、R5Is an alkane, R6Is hydrogen.
2. The iridium metal complex of claim 1 wherein R is1、R2、R3The substitution position is any position of the ring; r1The number of the substituents is 0-3, R2The number of substituents is 0-4, R3The number of the substituents is 0 to 4.
3. The iridium metal complex of claim 1 wherein alkyl is a straight chain alkyl, branched alkyl, cyclic alkyl, straight chain alkyl substituted with at least 1 substituent, branched alkyl substituted with at least 1 substituent, or cyclic alkyl substituted with at least 1 substituent; wherein, the substituent is one or more of halogen, deuterium, cyano, hydroxyl and sulfydryl independently.
4. An iridium metal complex according to claim 1, wherein the aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxy or mercapto.
5. An iridium metal complex according to claim 4, wherein the aromatic heterocyclic group is an unsubstituted heteroaryl group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the heteroaryl group is nitrogen, sulfur or oxygen; the substituents are independently selected from halogen, deuterium, amino, cyano, nitro, hydroxyl or mercapto.
6. A process for producing an iridium metal complex according to any one of claims 1 to 5, which comprises the steps of:
1) providing compound a and compound C, respectively, represented by the following structural formulae:
2) fully reacting the raw material A with iridium trichloride to prepare a bridging ligand intermediate B;
3) and fully reacting the intermediate B with the intermediate C to obtain the iridium metal complex shown in the chemical formula 1.
7. The method for producing an iridium metal complex according to claim 6, wherein the bridged ligand intermediate B has the structure:
8. an organic electroluminescent device comprising the iridium metal complex of claim 1 to 5, and further comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains the iridium metal complex of formula 1 of the present invention.
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