CN110862417A - Phosphorescent iridium complex, preparation method thereof and electroluminescent device - Google Patents
Phosphorescent iridium complex, preparation method thereof and electroluminescent device Download PDFInfo
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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Abstract
The invention discloses a phosphorescent iridium complex, a preparation method thereof and an electroluminescent device. According to the invention, the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained phosphorescent iridium complex is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved, the phosphorescent service life is delayed, and the driving voltage is reduced.
Description
Technical Field
The invention belongs to the field of organic photoelectric materials, and particularly relates to a novel efficient phosphorescent iridium complex, a preparation method thereof and an electroluminescent device.
Background
Organic Electroluminescent (OEL) or Organic Light-emitting Diodes (OLEDs) are an optical display technology using a thin film made of Organic materials having special physical properties and capable of generating transition luminescence under an external power source as a Light source. The OLED is used as a third generation display technology behind a cathode ray tube display (CRT) and a Liquid Crystal Display (LCD), has the excellent characteristics of high brightness, high efficiency, low energy consumption, low working voltage (3-10V), wide visual angle (170 degrees), rich and easily-regulated luminous color, high response speed (1 us) compared with the liquid crystal display, high definition, capability of manufacturing a large-area and flexible display panel and the like, and the luminous performance of the OLED is not limited by external conditions such as environment, humidity and the like.
Organic electroluminescence has been studied for a long time. The blue electroluminescence phenomenon based on anthrax crystal was first reported by Pope research group in 1963, but the driving voltage was as high as 400V due to the excessive crystal thickness (20um), and the light emission brightness and efficiency were low, so that no more attention was paid at that time. In 1965-1970, Helffich research group reported electroluminescence of aromatic compounds with condensed rings such as anthracene and naphthalene, but their driving voltage was higher than 100V, and has no practical application value. In 1982, the Vincet group adopted vacuum deposition method to obtain anthrax film with thickness reduced to 0.6um, so that the working voltage is reduced to about 30V, but the quantum efficiency is only 0.03%, and the film has poor quality, low electron injection efficiency, and is easily broken down.
In 1983, Partridge research groups discovered electroluminescence of non-conjugated polymers, but the resulting devices had low brightness. It can be seen that in 20 years from 60 to 80 of the 20 th century, the research on organic electroluminescence has not achieved remarkable results, and the development of OLEDs has been delayed. In 1987, Duncong cloud research team of Ischman Kodak company adopted vacuum deposition method to prepare multilayer organic electroluminescent device, and transparent and conductive ITO (steel tin oxide) coated glass was used as anodePolar aromatic diamine derivative (TPD) is used as hole transport layer and 8-hydroxyquinoline aluminum (Alq)3) As electron transporting and light emitting layer, Mg/Al (10:1) alloy as cathode. The device realizes high brightness (1000 cd-m)-2) Low driving voltage 10V), high efficiency (1.51 mW)-1) Good performance of.
Therefore, a novel phosphorescent iridium complex is developed to be used as a luminescent layer material, so that the performance of the electroluminescent device is better optimized.
Disclosure of Invention
The invention aims to provide a phosphorescent iridium complex, a preparation method thereof and an electroluminescent device.
The technical scheme adopted by the invention is as follows:
a phosphorescent iridium complex has a molecular structural general formula G as follows:
wherein m may be 0, 1 or 2, n may be 3, 2 or 1, and m + n is 3;
wherein R is1、R2、R3、R4、R5And R6Independently selected from hydrogen, deuterium atom, halogen, cyano, nitro, hydroxyl, amino, sulfonic group, sulfonyl, phosphoryl, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C2-C60 alkylene, substituted or unsubstituted C2-C60 alkyne, substituted or unsubstituted C4-C60 heterocyclic group, substituted or unsubstituted C10-C60 condensed ring group, and substituted or unsubstituted C5-C60 spiro ring group.
Wherein the atoms of the above groups or substituents may be deuterated;
wherein R is1、R2、R3、R4、R5、R6The position of the substituent is any position of the ring, R1、R2、R4And R6Represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent, R3And R5Represents a mono-substituent, a di-substituent or no substituent; r1、R2、R3、R4、R5And R6Any two adjacent substituents may also form a condensed ring or a heteroaromatic ring with the ring on which they are present, and the substituents which do not form a condensed ring or a heteroaromatic ring are preferably hydrogen, a deuterium atom, a substituted or unsubstituted C3-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C4-C60 heterocyclic group, a substituted or unsubstituted C8-C60 condensed ring group, a substituted or unsubstituted C5-C60 spiro ring group.
Halogen means fluorine, chlorine, bromine and iodine.
The alkyl is a straight-chain alkyl, a branched-chain alkyl, a cyclic alkyl, a straight-chain alkyl substituted by at least 1 substituent, a branched-chain alkyl substituted by at least 1 substituent or a cyclic alkyl substituted by at least 1 substituent; wherein the substituents are independently selected from deuterium, nitro, halogen, carbonyl, and combinations thereof.
The aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein, the substituent is independently selected from one or more of deuterium, nitro, halogen and carbonyl.
The aromatic heterocyclic group is an unsubstituted aromatic heterocyclic group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the aromatic heterocyclic group is nitrogen, sulfur or oxygen; the substituents are independently selected from deuterium, halogen, nitro.
R1、R2Independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C18 aromatic ring, a substituted or unsubstituted C4-C18 aromatic heterocycle, a substituted or unsubstituted C10-C18 condensed ring or a substituted or unsubstituted C10-C18 condensed ring with a substituent on the ringSubstituted C5-C18 spiro ring; the substituents on the foregoing substituents are selected from at least hydrogen, deuterium, nitro, halogen, cyano, carbonyl, and combinations thereof.
R1、R2、R3、R4、R5And R6Preferred are hydrogen, deuterium atoms, substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C3-C20 alkoxy groups, substituted or unsubstituted C4-C20 heterocyclic groups, substituted or unsubstituted C6-C20 aryl groups, and substituted or unsubstituted C10-C20 condensed ring groups.
The phosphorescent iridium complex has any one of structures shown as the following formulas G-1, G-2 and G-3:
in the above technical solution, it is most preferable that the phosphorescent iridium complex is selected from any one of the following structures:
some specific structural forms are listed above, but the series of phosphorescent iridium complexes are not limited to the above molecular structures, and other specific molecular structures can be obtained through simple transformation of some simple groups, substituted groups thereof and substitution positions, and are not described in detail herein.
The invention also provides two technical schemes of the preparation method of the phosphorescent iridium complex:
the method I comprises the following steps:
1) reacting a compound with a structure shown in a formula A1 with iridium trichloride to obtain a bridged ligand with a structure shown in a formula B1;
2) reacting the bridged ligand with the structure of the formula B1 with silver trifluoromethanesulfonate to obtain a bridged ligand with the structure of the formula C1;
3) and (3) reacting the bridging ligand with the structure of formula C1 with the ligand with the structure of formula D1 to obtain the phosphorescent iridium complex with the structure of formula G1.
The second method comprises the following steps:
1) reacting a compound with a structure shown in a formula A2 with iridium trichloride to obtain a bridged ligand with a structure shown in a formula B2;
2) reacting the bridged ligand with the structure of the formula B2 with silver trifluoromethanesulfonate to obtain a bridged ligand with the structure of the formula C2;
3) and (3) reacting the bridging ligand with the structure of formula C2 with the ligand with the structure of formula D2 to obtain the phosphorescent iridium complex with the structure of formula G2.
An electroluminescent device comprising the phosphorescent iridium complex. The organic electroluminescent device comprises: a first electrode, a second electrode and an organic layer disposed between the two electrodes, wherein the organic layer comprises the phosphorescent iridium complex of the present invention; the phosphorescent iridium complex is in a single form or is mixed with other substances and exists in an organic layer.
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 light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer with electron transport and electron injection functions.
The organic electroluminescent device comprises at least one functional layer of the phosphorescent iridium complex.
The organic electroluminescent device comprises a light-emitting layer, and the light-emitting layer contains the phosphorescent iridium complex.
The light emitting layer of the organic electroluminescent device comprises a main material and a doping material, wherein the doping material is the phosphorescent iridium complex, and the mixing ratio of the main material to the doping material is 90: 10-99.5: 0.5.
The device of the invention can be used for an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
The invention has the beneficial effects that:
the invention provides a novel efficient phosphorescent iridium complex, which is characterized in that specific heterocyclic ligands are selected for combination, the wavelength of a compound is adjusted, and the obtained phosphorescent iridium complex is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved, the phosphorescent service life is delayed, and the driving voltage is reduced.
The following will clearly and completely describe the technical solutions of 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 embodiments. All embodiments that can be obtained by a person skilled in the art based on the embodiments of the present invention without any inventive step are within the scope of the present invention.
Detailed Description
The following phosphorescent iridium complexes are taken as examples, and the preparation methods of the rest phosphorescent iridium complexes are similar and are not further exemplified.
Example 1: preparation of G-001
The first step is as follows:weighing A-001(64.5mmol, 10.00g) IrC1 of formula A under the protection of nitrogen3·3H2O (21.5mmo1, 7.58g) is put into a reaction system, a mixed solution of 300m1 ethylene glycol ethyl ether and 100m1 pure water is added, the mixture is refluxed for 24 hours under the protection of nitrogen, then the mixture is cooled to room temperature, precipitates are separated out, the precipitates are filtered by suction, and water, absolute ethyl alcohol and petroleum ether are used for washing and drying in sequence. This gave bridging ligand B-001 as a yellow powder (5.20g, 46.8% yield).
The second step is that: weighing bridging ligand B-001(4.66mmol, 5.00g), adding silver trifluoromethanesulfonate (10.25mmol, 2.69g), adding dichloromethane 100ml, adding methanol 40ml, refluxing under nitrogen protection for 24 hr, cooling to room temperature, and concentrating the filtrate to obtain solid. This gave bridged ligand C-001 as a yellow powder (3.4g, 50.9% yield).
The third step: weighing bridging ligand C-001(4.18mmol, 3.00g), adding ligand D-001(1.39mmol, 0.45g), adding 120ml of absolute ethanol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, and drying. The filtrate was subjected to silica gel column chromatography using methylene chloride as a solvent to concentrate a solid to precipitate, thereby obtaining a final yellow phosphorescent iridium complex G-001(0.7G, yield 62.5%).
HPLC purity greater than 99%.
Mass spectrum: calculated values: 808.96, respectively; test values are: 809.20.
elemental analysis:
calculated C, 65.33%; h, 3.74%; ir, 23.76%; n, 5.19%; o, 1.98%;
test value C, 65.30%; h, 3.72%; ir, 23.76%; n, 5.15%; o,1.94 percent.
Example 2: preparation of G-014
The first step is as follows: a-014(64.5mmol, 10.00g), IrC1, was weighed out under nitrogen protection3·3H2O (21.5mmo1, 7.58g) was put into the reaction system, and a mixed solution of 300m1 ethylene glycol ethyl ether and 100m1 purified water was added thereto under nitrogen atmosphereRefluxing under protection for 24 hr, cooling to room temperature to precipitate, vacuum filtering, washing with water, anhydrous alcohol and petroleum ether, and oven drying. Bridged ligand B-014(5.8g, 50.3% yield) was obtained as a yellow powder.
The second step is that: weighing bridging ligand B-014(4.66mmol, 5.00g), adding silver trifluoromethanesulfonate (10.25mmol, 2.69g), adding dichloromethane 100ml, adding methanol 40ml, refluxing under nitrogen protection for 24 hr, cooling to room temperature, and concentrating the filtrate to precipitate solid. The iridium complex bridged ligand C-014(3.2g, 47.9% yield) was obtained as a yellow powder.
The third step: weighing bridging ligand C-014(4.18mmol, 3.00g), adding ligand D-014(1.39mmol, 0.48g), adding 120ml of absolute ethanol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, and drying. The filtrate was subjected to silica gel column chromatography using methylene chloride as a solvent to concentrate a solid to precipitate, thereby obtaining a final yellow phosphorescent iridium complex G-014(0.6G, yield 50.8%).
HPLC purity greater than 99%;
mass spectrum: calculated values: 851.25, respectively; test values are: 851.04.
elemental analysis:
calculated C, 66.33%; h, 4.26%; ir, 22.59%; n, 4.94%; o, 1.88%;
test value C, 66.31%; h, 4.25%; ir, 22.58%; n, 4.91%; o,1.89 percent.
Example 3: preparation of G-022
The first step is as follows: formula A-022(33mmol, 10.00g), IrC1 was weighed under nitrogen protection3·3H2Adding O (11mmo1,3.87g) into a reaction system, adding a mixed solution of 300m1 ethylene glycol ethyl ether and 100m1 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, sequentially leaching with water, absolute ethyl alcohol and petroleum ether, and drying. The bridging ligand B-022(5.31g, 5g in 5 yield) was obtained as a yellow powder7％)。
The second step is that: weighing bridging ligand B-022(2.96mmol, 5.00g), adding silver trifluoromethanesulfonate (6.51mmol, 1.71g), adding 100ml of dichloromethane into the system, adding 40ml of methanol, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, and concentrating the filtrate of column chromatography (short column) until solid is separated out. Bridged ligand C-022 was obtained as a yellow powder (3.1g, 51% yield).
The third step: weighing bridging ligand C-022(2.93mmol, 3g), adding ligand D-022(0.97mmol, 0.17g), adding 120ml of absolute ethanol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, and drying. The filtrate was subjected to silica gel column chromatography using methylene chloride as a solvent to concentrate a solid to precipitate, thereby obtaining a final yellow phosphorescent iridium complex G-022(0.45G, yield 47.4%).
HPLC purity greater than 99%.
Mass spectrum: calculated values: 977.26, respectively; test values are: 977.17.
elemental analysis:
calculated C, 68.83%; h, 3.92%; ir, 19.67%; n, 4.30%; o, 3.27%;
test value C, 68.84%; h, 3.91%; ir, 19.65%; n, 4.28%; and 3.25 percent of O.
Example 4: preparation G-035
The first step is as follows: weighing the compound of formula A-035(29mmol, 10.00g), IrC1 under nitrogen protection3·3H2Adding O (9.7mmo1, 3.42g) into a reaction system, adding a mixed solution of 300m1 ethylene glycol ethyl ether and 100m1 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, sequentially leaching with water, absolute ethyl alcohol and petroleum ether, and drying. This gave bridging ligand B-035(6.30g, 70% yield) as a yellow powder.
The second step is that: weighing bridging ligand B-035(2.69mmol, 5.00g), adding silver trifluoromethanesulfonate (5.92mmol, 1.55g), adding dichloromethane 100ml, adding methanol 40ml, refluxing for 24 h under nitrogen protection, cooling to room temperature, and concentrating the filtrate of column chromatography (short column) until solid is separated out. This gave bridging ligand C-035(2.81g, 54.6% yield) as a yellow powder.
The third step: weighing the bridged ligand C-035(2.93mmol, 2.80g), adding the ligand D-035(0.98mmol, 0.16g), adding 120ml of absolute ethyl alcohol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol and drying. The filtrate was concentrated to precipitate a solid by column chromatography on silica gel using methylene chloride as a solvent to obtain the final yellow phosphorescent iridium complex G-035(0.6G, yield 43%).
HPLC purity greater than 99%;
mass spectrum: calculated values: 1061.35, respectively; test values are: 1061.32, respectively;
elemental analysis:
calculated C, 70.17%; h, 4.75%; ir, 18.11%; n, 3.96%; o, 3.01%;
test value C, 70.15%; h, 4.72%; ir, 18.05%; n, 3.93%; and O,3.04 percent.
Example 5: preparation of G-054
The first step is as follows: formula A-054(59mmol, 10.00g), IrC1 were weighed under nitrogen protection3·3H2O (19.7mmo1, 6.94g) is put into a reaction system, a mixed solution of 300m1 ethylene glycol ethyl ether and 100m1 pure water is added, the mixture is refluxed for 24 hours under the protection of nitrogen, then the mixture is cooled to room temperature, precipitates are separated out, the precipitates are filtered by suction, and water, absolute ethyl alcohol and petroleum ether are used for washing and drying in sequence. This gave bridging ligand B-054(5.2g, 46.8% yield) as a yellow powder.
The second step is that: weighing bridging ligand B-054(4.43mmol, 5.00g), adding silver trifluoromethanesulfonate (9.75mmol, 2.55g), adding dichloromethane 100ml, adding methanol 40ml, refluxing for 24 h under nitrogen protection, cooling to room temperature, and concentrating the filtrate of column chromatography (short column) until solid is separated out. The bridged ligand C-0-054(3.1g, 46.9% yield) was obtained as a yellow powder.
The third step: weighing bridging ligand C-054(4.16mmol, 3.1g), adding ligand D-054(1.39mmol, 0.45g), adding 120ml absolute ethyl alcohol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, and drying. The filtrate was subjected to silica gel column chromatography using methylene chloride as a solvent to concentrate a solid to precipitate, thereby obtaining a final yellow phosphorescent iridium complex G-054(0.4G, yield 33.8%).
HPLC purity greater than 99%;
mass spectrum: calculated values: 851.25, respectively; test values are: 851.16, respectively;
elemental analysis:
calculated C, 66.33%; h, 4.26%; ir, 22.59%; n, 4.94%; o, 1.88%;
test value C, 66.30%; h, 4.23%; ir, 22.58%; n, 4.96%; o,1.87 percent.
Example 6: preparation of G-060
The first step is as follows: weighing formula A-060(27mmol, 10.00g), IrC1 under nitrogen protection3·3H2Adding O (9mmo1, 3.17g) into a reaction system, adding a mixed solution of 300m1 ethylene glycol ethyl ether and 100m1 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, sequentially leaching with water, absolute ethyl alcohol and petroleum ether, and drying. The bridging ligand B-060 was obtained as a yellow powder (4.01g, 46% yield).
The second step is that: weighing bridging ligand B-060(2.09mmol, 4.00g), adding silver trifluoromethanesulfonate (4.60mmol, 1.21g), adding dichloromethane 100ml, adding methanol 40ml, refluxing under nitrogen protection for 24 h, cooling to room temperature, and concentrating the filtrate of column chromatography (short column) until solid is separated out. The bridging ligand C-060 was obtained as a yellow powder (3.10g, 65% yield).
The third step: weighing bridging ligand C-060(2.63mmol, 3.00g), adding ligand D-060(0.88mmol, 0.16g), adding 120ml of absolute ethyl alcohol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, and drying. The filtrate was subjected to silica gel column chromatography using methylene chloride as a solvent to concentrate a solid to precipitate, thereby obtaining the final yellow phosphorescent iridium complex G-060(0.4G, yield 41%).
HPLC purity greater than 99%;
mass spectrum: calculated values: 1106.42, respectively; test values are: 1106.38, respectively;
elemental analysis:
calcd C, 70.56%; h, 5.37%; ir, 17.37%; n, 3.80%; o, 2.89%;
test value C, 70.57%; h, 5.37%; ir, 17.37%; n, 3.80%; o,2.87 percent.
The synthesis methods of other phosphorescent iridium complexes G-003, G-009, G-011, G-014, G-015, G-020, G-022, G-030, G-035, G-043, G-048, G-054, G-060, G-075, G-080, G-085, G-090, G-092 and G-107 are the same as the above examples, which are not repeated herein, and the molecular formulas or mass spectra of other synthesized phosphorescent iridium complexes are shown in the following Table 1:
TABLE 1 phosphorescent Iridium Complex molecular formula and Mass Spectrometry
The invention also provides an electroluminescent device which is prepared by doping the phosphorescent iridium complex, and more particularly is prepared by the phosphorescent iridium complexes of the chemical formulas G-001, G-014, G022, G-035, G-054, G-060 and the like.
To further illustrate the present invention, the following more specific examples are set forth:
example 7: preparation of electroluminescent device by using phosphorescent iridium complex in Table 1
Coating with a thickness of
The ITO glass substrate is cleaned in distilled water for 2 times, ultrasonically cleaned for 30 minutes, and repeatedly cleaned with distilled waterUltrasonic cleaning for 10 minutes 2 times, after the completion of the cleaning with distilled water, sequentially ultrasonic cleaning with solvents such as isopropyl alcohol, acetone, and methanol, drying, transferring to a plasma cleaning machine, cleaning the substrate for 5 minutes, and transferring to a deposition machine. Firstly, evaporating 60nm on ITO (anode) ("2-TNATA"); hole injection layer evaporation (NPB)60 nm; the weight ratio of a compound 90:10 shown in the table 1 of a host substance ("CBP") and a doping substance of the luminous layer is mixed and evaporated for 30 nm; evaporating a hole blocking layer ("BALq") with the thickness of 10 nm; vapor deposition of electron transport layers (' Alq)3")40nm thickness; evaporating an electron injection Layer (LiF) by 0.2 nm; the evaporation cathode Al is 150nm, and the electroluminescent device is prepared by the method. The performance and the luminescence characteristics of the obtained electroluminescent device are tested, and a KEITHLEY 2400 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 phosphorescence service life.
Comparative example 1
An organic electroluminescent device was prepared in the same manner as in example 7, and the structure of the green light-doped compound of the light-emitting layer was as follows:
the same examination as in example 7 was performed on the prepared organic electroluminescent device, and the results are shown in table 2.
Table 2 test results of organic electroluminescent devices in example 7 and comparative example
As can be seen from Table 2, the organic electroluminescent device prepared using the compound provided by the present invention as a dopant material for the light emitting layer and the comparative compound Ir (ppy)3Compared with the electroluminescent device prepared by the doped material of the luminescent layer, the driving voltage is obviously reduced, the luminous efficiency and the service life are obviousAnd (4) improving.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come within the scope of the appended claims and their equivalents.
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 (14)
1. A phosphorescent iridium complex, characterized by: the molecular structure general formula G of the phosphorescent iridium complex is as follows:
wherein m may be 0, 1 or 2, n may be 3, 2 or 1, and m + n is 3;
wherein R is1、R2、R3、R4、R5And R6Independently selected from hydrogen, deuterium atom, halogen, cyano, nitro, hydroxyl, amino, sulfonic group, sulfonyl, phosphoryl, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C2-C60 alkylene, substituted or unsubstituted C2-C60 alkyne, substituted or unsubstituted C4-C60 heterocyclic group, substituted or unsubstituted C10-C60 condensed ring group, and substituted or unsubstituted C5-C60 spiro ring group.
2. The phosphorescent iridium complex of claim 1, wherein: the atoms of the above groups or substituents may be deuterated.
3. The phosphorescent iridium complex of claim 1, wherein: wherein R is1、R2、R3、R4、R5、R6The position of the substituent is any position of the ring, R1、R2、R4And R6Represents a mono-substituent, a di-substituent, a tri-substituent, a tetra-substituent or no substituent, R3And R5Represents a mono-substituent, a di-substituent or no substituent; r1、R2、R3、R4、R5And R6Any two adjacent substituents may also form a condensed ring or a heteroaromatic ring with the ring on which they are present, and the substituents which do not form a condensed ring or a heteroaromatic ring are preferably hydrogen, a deuterium atom, a substituted or unsubstituted C3-C60 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C4-C60 heterocyclic group, a substituted or unsubstituted C8-C60 condensed ring group, a substituted or unsubstituted C5-C60 spiro ring group.
4. The phosphorescent iridium complex of claim 1, wherein: the halogen refers to fluorine, chlorine, bromine and iodine.
5. The phosphorescent iridium complex of claim 1, wherein: the alkyl is a straight-chain alkyl, a branched-chain alkyl, a cyclic alkyl, a straight-chain alkyl substituted by at least 1 substituent, a branched-chain alkyl substituted by at least 1 substituent or a cyclic alkyl substituted by at least 1 substituent; wherein the substituents are independently selected from deuterium, nitro, halogen, carbonyl, and combinations thereof.
6. The phosphorescent iridium complex of claim 1, wherein: the aryl group is an unsubstituted aryl group or an aryl group substituted with at least 1 substituent; wherein, the substituent is independently selected from one or more of deuterium, nitro, halogen and carbonyl.
7. The phosphorescent iridium complex of claim 1, wherein: the aromatic heterocyclic group is an unsubstituted aromatic heterocyclic group or an aromatic heterocyclic group substituted with at least 1 substituent; wherein the heteroatom in the aromatic heterocyclic group is nitrogen, sulfur or oxygen; the substituents are independently selected from deuterium, halogen, nitro.
8. The phosphorescent iridium complex of claim 1, wherein: the R is1、R2Independently form a substituted or unsubstituted C3-C30 aliphatic ring, a substituted or unsubstituted C6-C18 aromatic ring, a substituted or unsubstituted C4-C18 aromatic heterocycle, a substituted or unsubstituted C10-C18 condensed ring or a substituted or unsubstituted C5-C18 spiro ring with a substituent on the ring; the substituents on the foregoing substituents are selected from at least hydrogen, deuterium, nitro, halogen, cyano, carbonyl, and combinations thereof.
9. The phosphorescent iridium complex of claim 1, wherein: r1、R2、R3、R4、R5And R6Is hydrogen, deuterium atom, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C3-C20 alkoxy, substituted or unsubstituted C4-C20 heterocyclic group, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C10-C20 condensed ring group.
10. A phosphorescent iridium complex, characterized by: the phosphorescent iridium complex has any one of structures shown as the following formulas G-1, G-2 and G-3:
11. the phosphorescent iridium complex of claim 1, wherein: the phosphorescent iridium complex is selected from any one of the following structures:
12. a method for preparing the phosphorescent iridium complex of claim 1, comprising the steps of:
1) reacting a compound with a structure shown in a formula A1 with iridium trichloride to obtain a bridged ligand with a structure shown in a formula B1;
2) reacting the bridged ligand with the structure of the formula B1 with silver trifluoromethanesulfonate to obtain a bridged ligand with the structure of the formula C1;
3) and (3) reacting the bridging ligand with the structure of formula C1 with the ligand with the structure of formula D1 to obtain the phosphorescent iridium complex with the structure of formula G1.
13. A method for preparing the phosphorescent iridium complex of claim 1, comprising the steps of:
1) reacting a compound with a structure shown in a formula A2 with iridium trichloride to obtain a bridged ligand with a structure shown in a formula B2;
2) reacting the bridged ligand with the structure of the formula B2 with silver trifluoromethanesulfonate to obtain a bridged ligand with the structure of the formula C2;
3) and (3) reacting the bridging ligand with the structure of formula C2 with the ligand with the structure of formula D2 to obtain the phosphorescent iridium complex with the structure of formula G2.
14. An electroluminescent device comprising the phosphorescent iridium complex of claim 1.
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