CN111116674A - Iridium metal complex luminescent material and preparation method and application thereof - Google Patents
Iridium metal complex luminescent material and preparation method and application thereof Download PDFInfo
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- CN111116674A CN111116674A CN201911376526.9A CN201911376526A CN111116674A CN 111116674 A CN111116674 A CN 111116674A CN 201911376526 A CN201911376526 A CN 201911376526A CN 111116674 A CN111116674 A CN 111116674A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- 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 an iridium metal complex luminescent material and a preparation method and application thereof, wherein the iridium metal complex luminescent material has a structural general formula
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an iridium metal complex luminescent material and a preparation method and application thereof.
Background
The organic electroluminescence technology is a latest generation display technology, and a light-emitting device prepared from an organic light-emitting material has the advantages of light weight, thinness, flexibility and the like in appearance, and particularly can be prepared into a flexible device which cannot be compared with other light-emitting materials. In the past decade, this technology has achieved some success on the way to commercialization, for example, organic electroluminescent diodes (OLEDs) have been applied to advanced displays for smart phones, televisions and digital cameras. Organic electroluminescent materials are the core and foundation of electroluminescent devices. The development of new materials is a source 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. Conventional OLEDs can be classified into fluorescent and phosphorescent types. Compared with fluorescent OLEDs (theoretical luminous efficiency is 25% at the highest), phosphorescent OLEDs (theoretical luminous efficiency 100%) are the mainstream direction for OLED technology research and development due to their higher luminous efficiency.
The light emitting material of the organic light emitting diode is mainly a phosphorescent light emitting material, wherein independent light emitting of three primary colors of red, blue and green is the most adopted color mode at present, and the technical key point is to improve the light color purity and efficiency of the light emitting material. Therefore, in recent years, research into organic phosphorescent materials has been conducted, and the most of them is a metal iridium metal complex.
However, the prior art of phosphorescent materials is still in need of improvement and development in terms of reducing the cost of the material preparation process, improving the basic photoelectric properties of the material, and improving the overall tolerance and weather resistance of the material after device integration. Therefore, the development of a material with high luminous efficiency and long lifetime is a technical problem to be solved.
Disclosure of Invention
In view of the above, the present invention provides an iridium metal complex luminescent material, and a preparation method and an application thereof, and the iridium metal complex luminescent material provided by the present invention, as a luminescent material of an organic electroluminescent device, can improve the luminous efficiency of the device and prolong the service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
an iridium metal complex luminescent material is characterized in that the structural general formula of the iridium metal complex luminescent material is shown as chemical formula 1:
wherein:
m represents an integer of 0 to 2, n represents an integer of 1 to 3, and m + n is 3;
x independently represents O or S;
R1～R5each independently represents hydrogen, deuterium, halogen, cyano, silyl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, thio, sulfinyl, sulfonyl, phosphino, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C1～C8Alkoxy, substituted or unsubstituted C2～C6Alkenyl, substituted or unsubstituted C2～C6Alkynyl, C1～C30Alkylamino radical, C6～C30Arylamino, substituted or unsubstituted C6～C30Aryl radical, C6～C30Aryloxy, substituted or unsubstituted C4～C12A heteroaryl group;
R1～R5the substituent position of (A) is any position of the ring, R1、R2、R4、R5The number of substituents is 0 to 4, R3The number of the substituents is 0 to 2.
Preferably, R1～R5Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C4～C12A heteroaryl group.
Preferably, said R is1～R3Each independently of the others forms a substituted or unsubstituted C with the ring3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaryl group.
Preferably, said R is4～R5Each independently of the others forms a substituted or unsubstituted C with the ring3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaryl group.
Preferably, said R is1～R3Form a substituted or unsubstituted C with each other3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaryl group.
Preferably, said R is4～R5Form a substituted or unsubstituted C with each other3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaryl group.
Preferably, said R is1～R3Each independently of the others of the ring to form a substituted or unsubstituted C3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaryl group.
Preferably, said R is4～R5Each independently of the others of the ring to form a substituted or unsubstituted C3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaryl group.
Preferably, the alkyl is a straight-chain alkyl or branched-chain alkyl; the alkyl group is preferably C1～C8Alkyl, more specifically including methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl.
Preferably, the cycloalkyl group includes monocyclic, polycyclic, spiro alkyl; the cycloalkyl group is preferably C3～C15More specifically including cyclopropyl, cyclopentyl, cyclohexyl, adamantylamino.
Preferably, the heterocycloalkyl group is a cycloalkyl group containing at least one heteroatom, preferably a heterocycloalkyl group containing 3 to 7 ring atoms including at least one said heteroatom, and including cyclic amines, more particularly including morpholinyl, piperidinyl, pyrrolidinyl, tetrahydrofuran, tetrahydropyran, said heteroatom being selected from one or a combination of more of N, O, S, P, B, Si, Se, Ge; the heteroatoms are preferably N, O, S in combination of one or more.
Preferably, the aryl group is a monocyclic aryl group and a polycyclic aryl group; the polycyclic aryl has more than two rings wherein two carbons are common to two adjoining rings, at least one of the rings is aryl and the other rings are selected from the group consisting of cycloalkyl, cycloalkenyl, aryl, heteroaryl, and combinations of one or more thereof. The aryl group is preferably C6～C20Aryl groups, more specifically including benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorene. Wherein the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. When the fluorenyl group is substituted, it may include spirofluorenyl groups such as
And substituted fluorenyl radicals such as
(9, 9-dimethylfluorenyl group) and
(9, 9-diphenylfluorenyl).
Preferably, the heteroaryl is monocyclic heteroaryl and polycyclic aryl; the monocyclic heteroaryl group has a monocyclic heteroaromatic group of 1,2 or 3 heteroatoms, including pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine and pyrimidine; the polycyclic heteroaryl has more than two rings wherein two atoms are common to two adjoining rings, the atoms being one or a combination of two of carbon atoms, heteroatoms, at least one of the rings being heteroaryl and the other rings being selected from one or a combination of more of cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl; the heteroatom is selected from one or more of N, O, S, P, B, Si, Se and Ge, and is preferably N, O, S.
Preferably, R1～R5Each independently substituted with one or more substituents independently representing hydrogen, deuterium, halogen, acyl, carbonyl, carboxylic acid group, ether group, ester group, nitrile group, thio group, sulfinyl group, sulfonyl group, phosphino group, alkyl group, alkoxy group, aryloxy group, alkylamino group, arylamino group, silane group, alkenyl group, alkynyl group, aryl group, heteroaryl group, spiro ring group; the substituents are preferably hydrogen, halogen, deuterium, alkylamino, arylamino, cyano, nitro, hydroxy, mercapto, alkyl.
The "substitution" in the above technical scheme means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and the position of substitution is not limited as long as the position is a position at which the hydrogen atom is substituted (i.e., a position at which the substituent may be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.
Preferably, R1～R5The following groups are preferred:
wherein
Is the attachment location.
Preferably, the iridium metal complex luminescent material shown in chemical formula 1 has a specific structural formula:
the invention also provides a preparation method of the iridium metal complex luminescent material, when m is 2 and n is 1, the structure of the chemical formula 1 is shown as the formula I, and the specific synthesis steps of the formula I are as follows:
s1, reacting the compound with the structure of the formula A-1 with iridium trichloride under the protection of inert gas, and after the reaction is finished, cooling, precipitating, washing and drying to obtain the compound with the structure of the formula B-1;
s2, under the protection of inert gas, reacting the compound with the structure shown in the formula B-1 with silver trifluoromethanesulfonate and methanol, and after the reaction is finished, cooling, carrying out column chromatography and concentrating to obtain the compound with the structure shown in the formula C-1;
s3, under the protection of inert gas, carrying out reflux reaction on the compound with the structure of the formula C-1 and the compound with the structure of the formula D-1 in absolute ethyl alcohol for 20-24h, and after the reaction is finished, carrying out suction filtration, alcohol washing, drying, column chromatography and concentration to obtain the compound with the structure of the formula I;
the synthetic route for compounds of the structure of formula I is as follows:
when m is 1 and n is 2, the structure of formula 1 is shown as formula II, and the specific synthesis steps of formula II are as follows:
y1, reacting the compound with the structure of the formula A-2 with iridium trichloride under the protection of inert gas, and after the reaction is finished, cooling, precipitating, washing and drying to obtain the compound with the structure of the formula B-2;
y2, under the protection of inert gas, reacting the compound with the structure of the formula B-2 with silver trifluoromethanesulfonate and methanol, and after the reaction is finished, cooling, carrying out column chromatography and concentrating to obtain the compound with the structure of the formula C-2;
y3, under the protection of inert gas, carrying out reflux reaction on the compound with the structure of the formula C-2 and the compound with the structure of the formula D-2 in absolute ethyl alcohol for 20-24h, and after the reaction is finished, carrying out suction filtration, alcohol washing, drying, column chromatography and concentration to obtain the compound with the structure of the formula II;
the synthetic route for the compound of formula II is as follows:
when m is 0 and n is 3, the structure of formula 1 is shown as formula III, and the specific synthesis steps of formula III are as follows:
k1, reacting the compound with the structure of the formula A-3 with iridium trichloride under the protection of inert gas, and after the reaction is finished, cooling, precipitating, washing and drying to obtain the compound with the structure of the formula B-3;
k2, under the protection of inert gas, reacting the compound with the structure of the formula B-3 with silver trifluoromethanesulfonate and methanol, and after the reaction is finished, cooling, carrying out column chromatography and concentrating to obtain the compound with the structure of the formula C-3;
k3, under the protection of inert gas, carrying out reflux reaction on the compound with the structure of the formula C-3 and the compound with the structure of the formula D-3 in absolute ethyl alcohol for 20-24h, and after the reaction is finished, carrying out suction filtration, alcohol washing, drying, column chromatography and concentration to obtain the compound with the structure of the formula III;
the synthetic route for the compound of formula III is as follows:
preferably, in the step S1, the reaction molar ratio of the compound with the structure of the formula A-1 to the iridium trichloride is 1 (0.3-0.5).
Preferably, in the step Y1, the reaction molar ratio of the compound with the structure of the formula A-2 to the iridium trichloride is 1 (0.3-0.5).
Preferably, in the step K1, the reaction molar ratio of the compound with the structure of the formula A-3 to the iridium trichloride is 1 (0.3-0.5).
Preferably, in the step S2, the reaction molar ratio of the compound with the structure of the formula B-1 to the silver trifluoromethanesulfonate is 1 (2-3).
Preferably, in the step Y2, the reaction molar ratio of the compound with the structure of the formula B-2 to the silver trifluoromethanesulfonate is 1 (2-3).
Preferably, in the step K2, the reaction molar ratio of the compound with the structure of the formula B-3 to the silver trifluoromethanesulfonate is 1 (2-3).
Preferably, in the step S3, the reaction molar ratio of the compound with the structure of the formula C-1 to the compound with the structure of the formula D-1 is 1 (2-3).
Preferably, in the step Y3, the reaction molar ratio of the compound with the structure of the formula C-2 to the compound with the structure of the formula D-2 is 1 (2-3).
Preferably, in the step K3, the reaction molar ratio of the compound with the structure of the formula C-3 to the compound with the structure of the formula D-3 is 1 (2-3).
Preferably, in the step S1, the step Y1, and the step K1, the post-processing procedure is: and cooling the reaction liquid to room temperature, separating out a precipitate, carrying out suction filtration on the precipitate, and washing and drying the precipitate by using water, absolute ethyl alcohol and petroleum ether in sequence to obtain a yellow powder bridged ligand compound of the formula B-1/B-2/B-3.
Preferably, in the step S2, the step Y2, and the step K2, the post-processing procedure is: and cooling the reaction liquid to room temperature, and concentrating the filtrate of column chromatography (short column) until solid is separated out to obtain the yellow powder iridium metal complex intermediate compound of formula C-1/C-2/C-3.
Preferably, in the step S3, the step Y3, and the step K3, the post-processing procedure is: and (3) carrying out suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, carrying out silica gel column chromatography, and concentrating the filtrate to precipitate a solid to obtain a final yellow compound, namely the target compound of the formula I/II/III.
The invention further provides application of the iridium metal complex luminescent material in an organic electroluminescent device.
The present invention also provides an organic electroluminescent device comprising the iridium metal complex represented by chemical formula 1 of the present invention.
The organic electroluminescent device includes: a first electrode, a second electrode, and an organic layer having at least one, the organic layer being interposed between the first electrode and the second electrode, wherein at least one layer of the organic layer contains an iridium metal complex represented by chemical formula 1 of the present invention; the iridium metal complex of chemical formula 1 of the present invention may be present in the organic material layer in a single form or in a mixture with other materials.
Preferably, the organic layer includes at least one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport technologies, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection technologies.
Preferably, the organic electroluminescent device includes a light emitting layer containing the iridium metal complex of formula 1 of the present invention.
Preferably, the light emitting layer includes a host material including a fluorescent host and a phosphorescent host, and a dopant material that is an iridium metal complex represented by chemical formula 1 of the present invention.
Preferably, the mass ratio of the host material to the dopant material is (90:10) - (99.5: 0.5).
The invention further provides application of the organic electroluminescent device in an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
According to the technical scheme, compared with the prior art, the iridium metal complex luminescent material and the preparation method and application thereof provided by the invention have the following beneficial effects:
(1) according to the iridium metal complex luminescent material provided by the invention, the specific heterocyclic complex 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, and the service life is long.
(2) The preparation method of the iridium metal complex luminescent material provided by the invention has the advantages of simple and efficient process and high purity of the prepared product.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious 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
The synthesis of the compound F002 comprises the following specific steps:
s1, weighing A002(64.43mmol) and IrCl under the protection of nitrogen3·3H2O (21.48mmo1) is put into a reaction system, a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified 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 to obtain bridging ligand B002(5.8g, the yield is 50.4%) of yellow powder.
S2, weighing intermediate B002(4.66mmol), adding silver trifluoromethanesulfonate (14mmol), adding 100mL of dichloromethane into the system, adding 40mL of methanol, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, concentrating the filtrate of column chromatography (short column) until solid is separated out, and obtaining iridium complex intermediate C002(5.8g, yield 87.4%) as yellow-green powder.
S3, weighing intermediate C002(7.03mmol), adding ligand D002(21.08mmol), adding 120mL of absolute ethyl alcohol into the system, refluxing for 24 hours under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, performing silica gel column chromatography, concentrating the filtrate until solid is separated out to obtain the final yellow compound F002(1.87g, the yield is 34.4%) with the HPLC purity of more than 99%, wherein the mass spectrum and element analysis results of the compound F002 are as follows:
mass spectrum calculated 772.93; test value 773.20;
element analysis, calculated value is C: 63.71%; 3.91 percent of H; 5.44 percent of N; 2.07 percent of O; 24.87 percent of Ir; the test value is C: 63.72%; h, 3.92 percent; 5.43 percent of N; 2.08 percent of O; 24.85 percent of Ir.
Example 2
The synthesis of the compound F008 comprises the following specific steps:
s1, weighing A008(64.43mmol) and IrCl under the protection of nitrogen3·3H2O (21.48mmo1) is put into a reaction system, 300mL of mixed solution of ethylene glycol ethyl ether and 100mL of purified water is added, the mixture is refluxed for 24 hours under the protection of nitrogen, then 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 to obtain bridging ligand B008(5.8g, the yield is 50.4%) which is yellow powder.
S2, weighing intermediate B008(4.66mmol), adding silver trifluoromethanesulfonate (14mmol), adding 100mL of dichloromethane into the system, adding 40mL of methanol, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, concentrating the filtrate of column chromatography (short column) until solid is separated out, and obtaining iridium complex intermediate C008(5.8g, yield 87.4%) as yellow-green powder.
S3, weighing intermediate C008(7.03mmol), adding ligand D008(21.08mmol), adding 120mL of absolute ethyl alcohol into the system, refluxing for 24 hours under the protection of nitrogen, performing suction filtration, washing with alcohol, drying, using dichloromethane as a solvent, performing silica gel column chromatography, concentrating the filtrate until solid is separated out to obtain the final yellow compound F008(2.03g, the yield is 36.08%) with the HPLC purity of more than 99%, wherein the mass spectrum and the elemental analysis result of the compound F008 are as follows:
mass spectrum calculated 800.98; test value 801.23;
element analysis, calculated value is C: 64.48%; 4.28 percent of H; 5.25 percent of N; 2.00 percent of O; 24.00 percent of Ir; the test value is C: 64.49%; 4.29 percent of H; 5.24 percent of N; 2.01 percent of O; 23.98 percent of Ir.
Example 3
The synthesis of the compound F017 comprises the following specific steps:
s1, weighing A017(59.09mmol) and IrCl under the protection of nitrogen3·3H2O (19.7mmol) is put into a reaction system, a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified 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 the obtained product is washed and dried by water, absolute ethyl alcohol and petroleum ether in sequence to obtain yellow powder of bridging ligand B017(5.4g, the yield is 48.6%).
S2, weighing intermediate B017(4.43mmol), adding silver trifluoromethanesulfonate (13.3mmol), 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 a column chromatography (short column) filtrate until solid is separated out to obtain iridium complex intermediate C017(5.2g, yield 79.3%) as yellow green powder.
S3, weighing intermediate C017(6.76mmol), adding ligand D017(20.28mmol), adding 120mL of absolute ethyl alcohol into the system, refluxing for 24 hours 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 until solid is separated out to obtain a final yellow compound F017(1.76g, the yield is 32.51%) with HPLC purity of more than 99%, wherein the mass spectrum and element analysis results of the compound F017 are as follows:
mass spectrum calculated 800.98; test value 801.23;
element analysis, calculated value is C: 64.48%; 4.28 percent of H; 5.25 percent of N; 2.00 percent of O; 24.00 percent of Ir; the test value is that C is 64.50 percent; 4.26 percent of H; 5.27 percent of N; 2.01 percent of O; 23.99 percent of Ir.
Example 4
The synthesis of compound F037 comprises the following specific steps:
y1, weighing A037(34.8mmol) and IrCl under the protection of nitrogen3·3H2O (11.6mmol) is put into a reaction system, a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified water is added, the mixture is refluxed for 24 hours under the protection of nitrogen, and then the mixture is cooled to a roomWhen the temperature is high, a precipitate is separated out, the precipitate is filtered by suction, washed by water, absolute ethyl alcohol and petroleum ether in sequence and dried to obtain bridging ligand B037(7.5g, the yield is 40.39%) of yellow powder.
Y2, weighing intermediate B037(4.37mmol), adding silver trifluoromethanesulfonate (13.12mmol), 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 to obtain iridium complex intermediate C037(3.8g, yield 89.03%) as yellow-green powder.
Y3, weighing intermediate C037(3.07mmol), adding ligand D037(9.22mmol), adding 120mL of absolute ethanol into the system, refluxing for 24 hours 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 until solid is separated out to obtain a final yellow compound F037(1.1g, the yield is 38.94%) with the HPLC purity of more than 99%, wherein the mass spectrum and the elemental analysis result of the compound F037 are as follows:
mass spectrum calculated 919.27; test value 919.12;
elemental analysis, calculated value is 66.65 percent of C; 4.39 percent of H; 4.57 percent of N; 3.48 percent of O; 20.91 percent of Ir; the test value is 66.66 percent of C; 4.40 percent of H; 4.55 percent of N; 3.49 percent of O; 20.90 percent of Ir.
Example 5
The synthesis of the compound F047 comprises the following specific steps:
y1, weighing A047(36.59mmol) and IrCl under the protection of nitrogen3·3H2O12.20mmol) in a reaction system, adding a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified water, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, separating out a precipitate, filtering the precipitate, washing and drying with water, absolute ethyl alcohol and petroleum ether in sequence to obtain yellow powder of bridging ligand B047(6.8g, the yield is 36.10%).
Y2, weighing intermediate B047(3.88mmol), adding silver trifluoromethanesulfonate (11.65mmol), 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 to obtain iridium complex intermediate C047(3g, yield 81.47%) as yellow green powder.
Y3, weighing intermediate C047(3.16mmol), adding ligand D047(9.49mmol), adding 120mL of absolute ethanol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, drying, using dichloromethane as a solvent, carrying out silica gel column chromatography, concentrating the filtrate until solid is separated out to obtain the final yellow compound F047(1.1g, yield 37.82%), HPLC purity is more than 99%, and the results of mass spectrum and element analysis of the compound F047 are as follows:
mass spectrum calculated 919.27; test value 919.12;
elemental analysis, calculated value is 66.65 percent of C; 4.39 percent of H; 4.57 percent of N; 3.48 percent of O; 20.91 percent of Ir; the test value is 66.66 percent of C; 4.40 percent of H; 4.55 percent of N; 3.49 percent of O; 20.90 percent of Ir.
Example 6
The synthesis of the compound F061 comprises the following specific steps:
y1, weighing A061(31.7mmol) and IrCl under the protection of nitrogen3·3H2O (10.57mmol) is put into a reaction system, a mixed solution of 300mL of ethylene glycol ethyl ether and 100mL of purified 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 to obtain bridging ligand B061(5.8g, the yield is 32.04%) of yellow powder.
Y2, weighing intermediate B061(2.94mmol), adding silver trifluoromethanesulfonate (8.83mmol), adding 100mL of dichloromethane into the system, adding 40mL of methanol, refluxing for 24 hours under the protection of nitrogen, cooling to room temperature, concentrating the filtrate of column chromatography (short column) until solid is separated out, and obtaining iridium complex intermediate C061(2.4g, yield 79.01%) as yellow-green powder.
Y3, weighing intermediate C061(1.94mmol), adding ligand D061(5.81mmol), adding 120mL of absolute ethyl alcohol into the system, refluxing for 24 hours under the protection of nitrogen, filtering, washing with alcohol, drying, using dichloromethane as a solvent, carrying out silica gel column chromatography, concentrating the filtrate until solid is separated out to obtain the final yellow compound F061(0.8g, the yield is 40.03%), wherein the HPLC purity is more than 99%, and the mass spectrum and the element analysis result of the compound F061 are as follows:
mass spectrum calculated 1031.40; the test value was 1031.33.
Elemental analysis, calculated value is 68.71 percent of C; 5.47 percent of H; 4.07 percent of N; 3.10 percent of O; 18.64 percent of Ir; the test value is 68.70 percent of C; 5.48 percent of H; 4.09 percent of N; 3.09 percent of O; 18.63 percent of Ir.
Examples 7 to 18
The target compounds of examples 7 to 18 were synthesized according to the synthesis method of example 1, with the results of FD-MS (mass spectrometry) shown in Table 1, by replacing the corresponding reactants only.
TABLE 1 FD-MS results for the target compounds of examples 7 to 18
The present invention also provides an organic electroluminescent device comprising the iridium metal complex represented by chemical formula 1 of the present invention.
The organic electroluminescent device includes: a first electrode, a second electrode, and one or more organic layers interposed between the two electrodes, wherein one or more of the organic layers comprise an iridium metal complex represented by chemical formula 1 of the present invention; the iridium metal complex of chemical formula 1 of the present invention may be present in the organic material layer in a single form or in a mixture 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 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 includes at least one functional layer containing the iridium metal complex of the present invention represented by chemical formula 1. An organic electroluminescent device includes a light emitting layer containing an iridium metal complex represented by chemical formula 1 of the present invention.
The light emitting layer of the organic electroluminescent device includes a host material and a dopant material, the host material includes a fluorescent host and a phosphorescent host, the dopant material is an iridium metal complex represented by chemical formula 1 of the present invention, and the mixing ratio of the host material and the dopant material of the light emitting layer is (90:10) - (99.5:0.5), but is not limited thereto.
The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, however, the structure is not limited thereto, and the organic material layer may have a single-layer structure. In manufacturing the organic light emitting device, the compound based on chemical formula 1 may be formed into an organic material layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, etc., but is not limited thereto.
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.
In the above organic electroluminescent device, as the anode material, a material having a large work function is generally preferred so that holes are smoothly injected into the organic material layer. Specific examples of anode materials that can be used in the context of the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, such as ZnO: Al or SnO2: Sb; conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
In the above organic electroluminescent device, as a cathode material, a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF/Al or LiO 2/Al; and the like, but are not limited thereto.
In the above organic electroluminescent device, the hole injecting material is a material that advantageously receives holes from the anode at a low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and polyaniline-and polythiophene-based conductive polymer, and the like, but are not limited thereto, and may further include another compound capable of p-doping.
In the above organic electroluminescent device, the hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and a material having high hole mobility is suitable. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.
In the above organic electroluminescent device, the electron blocking layer may be provided between the hole transport layer and the light emitting layer. As the electron blocking layer, a material known in the art, for example, an arylamine-based organic material, may be used.
In the above organic electroluminescent device, the light emitting layer may emit red, green or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in a visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq3), carbazole-based compounds, dimeric styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole/benzothiazole/benzimidazole-based compounds, poly (p-phenylene vinylene) (PPV) -based polymers, spiro compounds, polyfluorenes, rubrenes, and the like, but are not limited thereto.
In the above organic electroluminescent device, the host material of the light-emitting layer includes a condensed aromatic ring derivative, a heterocyclic ring-containing compound, and the like. Specifically, the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocycle-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like, however, the material is not limited thereto.
An iridium-based complex used as a dopant of a light emitting layer, which includes the compound represented by chemical formula 1 in the present invention.
In the above organic electroluminescent device, the hole blocking layer may be disposed between the electron transport layer and the light emitting layer, and a material known in the art, for example, a triazine-based compound may be used.
In the above organic electroluminescent device, the electron transport layer may function to facilitate electron transport. The electron transport material is a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer, and a material having high electron mobility is suitable. Specific examples thereof include: al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavone-metal complexes, and the like; but is not limited thereto. The thickness of the electron transport layer may be 1nm to 50 nm. The electron transport layer having a thickness of 1nm or more has an advantage of preventing the electron transport property from being degraded, and the electron transport layer having a thickness of 50nm or less has an advantage of preventing the driving voltage for enhancing electron transfer from being increased due to the electron transport layer being too thick.
In the above organic electroluminescent device, the electron injection layer may function to facilitate electron injection. The electron-injecting material is preferably a compound of: it has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injection layer, and, in addition, has an excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone and the like and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives and the like, but are not limited thereto.
The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double-side emission type, depending on the material used.
Example 19
The embodiment provides an organic electroluminescent device, which comprises a substrate, an anode layer arranged on the substrate, a hole injection layer arranged on the anode layer, a hole transport layer arranged on the hole injection layer, an organic light emitting layer arranged on the hole transport layer, an electron transport layer arranged on the organic light emitting layer, an electron injection layer arranged on the electron transport layer and a cathode layer arranged on the electron injection layer.
The preparation method of the organic electroluminescent device comprises the following steps:
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
The host species 4,4'-N, N' -Biphenyldicarbazole ("CBP") and the dopant species F002 were present in a weight ratio of 95:5Specific mixing evaporation
Vapor deposition of electron transport layer Alq3"
Evaporation of electron injection layer LiF
Deposition cathode Al
And (4) preparing the organic electroluminescent device.
By referring to the above method, F002 was replaced with F003, F008, F010, F013, F017, F022, F029, F034, F037, F041, F044, F047, F053, F054, F061, and F068, respectively, to prepare organic electroluminescent devices of the corresponding compounds.
Comparative example 1
An organic electroluminescent device was fabricated in the same manner as in example 19, except that the dopant compound F002 of the organic light-emitting layer was replaced with the compound Ir (ppy)3The resulting organic electroluminescent device, Compound Ir (ppy)3The structural formula of (A) is as follows:
to further illustrate the luminescence properties of the novel iridium complex as a phosphorescent material, the devices obtained in example 19 and comparative example 1 were tested for their luminescence properties, and the results of driving voltage, luminescence brightness, and luminescence efficiency were evaluated using a KEITHLEY model 2400 source measuring unit, a CS-2000 spectroradiometer, and are shown in table 2.
Table 2 test results of organic electroluminescent devices in example 19 and comparative example 1
As can be seen from Table 2, the light-emitting luminance was 5000cd/cm2Compared with the comparative example 1, the driving voltage of the device provided by the invention is 3.4-4.6V and is obviously lower than that of the comparative example 1, the efficiency (34.6-39.6) is far higher than that of the comparative example 1, and the service life (487-631) is 8-11 times that of the comparative example 1, so that the organic electroluminescent device prepared by using the compound provided by the invention as a luminescent layer doping material is obviously lower in driving voltage and remarkably improved in luminescent efficiency and service life compared with the organic electroluminescent device prepared by using a comparative compound Ir (ppy)3 as a luminescent layer doping material.
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 (10)
1. An iridium metal complex luminescent material is characterized in that the structural general formula of the iridium metal complex luminescent material is shown as chemical formula 1:
wherein:
m is an integer of 0-2, n is an integer of 1-3, and m + n is 3;
x independently represents O or S;
R1～R5each independently represents hydrogen, deuterium, halogen, cyano, silyl, acyl, carbonyl, carboxylic acid group, ester group, nitrile group, thio, sulfinyl, sulfonyl, phosphino, substituted or unsubstituted C1～C30Alkyl, substituted or unsubstituted C3～C30Cycloalkyl, substituted or unsubstituted C3～C30Heterocycloalkyl, substituted or unsubstituted C1～C8Alkoxy, substituted or unsubstituted C2～C6Alkenyl, substituted or unsubstituted C2～C6Alkynyl, substituted or unsubstituted C1～C30Alkylamino, substituted or unsubstituted C6～C30Arylamino, substituted or unsubstituted C6～C30Aryl, substituted or unsubstituted C6～C30Aryloxy, substituted or unsubstituted C4～C12A heteroaryl group;
R1～R5the substituent position of (A) is any position of the ring, R1、R2、R4、R5The number of substituents is 0 to 4, R3The number of the substituents is 0 to 2.
2. The iridium complex luminescent material as claimed in claim 1, wherein R is1～R5Each independently of the others forms a substituted or unsubstituted C with the ring3～C30Cycloalkanes, substituted or unsubstituted C3～C30Heterocycloalkanes, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaromatic ring.
3. The iridium complex luminescent material as claimed in claim 1, wherein R is1～R3Form a substituted or unsubstituted C with each other3～C30Cycloalkane, to getSubstituted or unsubstituted C3～C30Heterocycloalkanes, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaromatic ring;
the R is4～R5Form a substituted or unsubstituted C with each other3～C30Cycloalkanes, substituted or unsubstituted C3～C30Heterocycloalkanes, substituted or unsubstituted C6～C18Aromatic ring, substituted or unsubstituted C4～C18A heteroaromatic ring.
4. The iridium complex light-emitting material according to claim 1, wherein the heterocycloalkyl group is a heterocycloalkyl group having 3 to 7 ring atoms and containing at least one hetero atom, and includes a cyclic amine;
the heteroaryl is monocyclic heteroaryl and polycyclic aryl;
the monocyclic heteroaryl group is a monocyclic heteroaromatic group having 1 to 3 heteroatoms;
the polycyclic heteroaryl has two or more rings in which two atoms are common to two adjoining rings, the atoms being one or a combination of two of carbon atoms, heteroatoms, at least one of the rings being heteroaryl and the other rings being selected from one or a combination of more of cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl;
the heteroatom is selected from one or more of N, O, S, P, B, Si, Se and Ge.
5. The iridium complex light-emitting material according to claim 1, wherein the aryl group is a monocyclic aryl group and a polycyclic aryl group; the polycyclic aryl has two or more rings wherein two carbons are common to two adjoining rings, at least one of the rings is aryl and the other rings are selected from the group consisting of cycloalkyl, cycloalkenyl, aryl, heteroaryl, and combinations of one or more thereof.
6. The iridium metal complex luminescent material according to claim 1,R1～R5each independently substituted with one or more substituents independently representing hydrogen, deuterium, halogen, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, thio, sulfinyl, sulfonyl, phosphino, alkyl, alkoxy, aryloxy, alkylamino, arylamino, silane, alkenyl, alkynyl, aryl, heteroaryl, spiro ring.
7. The iridium complex luminescent material of claim 1, wherein R is1～R5Selected from the following groups:
wherein
Is the attachment location.
8. The preparation method of the iridium metal complex luminescent material as claimed in any one of claims 1 to 7, wherein when m is 2 and n is 1, the structure of chemical formula 1 is shown as formula I, and the specific synthesis steps of formula I are as follows:
s1, reacting the compound with the structure of the formula A-1 with iridium trichloride under the protection of inert gas, and after the reaction is finished, cooling, precipitating, washing and drying to obtain the compound with the structure of the formula B-1;
s2, under the protection of inert gas, reacting the compound with the structure shown in the formula B-1 with silver trifluoromethanesulfonate and methanol, and after the reaction is finished, cooling, carrying out column chromatography and concentrating to obtain the compound with the structure shown in the formula C-1;
s3, under the protection of inert gas, carrying out reflux reaction on the compound with the structure of the formula C-1 and the compound with the structure of the formula D-1 in absolute ethyl alcohol for 20-24h, and after the reaction is finished, carrying out suction filtration, alcohol washing, drying, column chromatography and concentration to obtain the compound with the structure of the formula I;
the synthetic route for compounds of the structure of formula I is as follows:
when m is 1 and n is 2, the structure of formula 1 is shown as formula II, and the specific synthesis steps of formula II are as follows:
y1, reacting the compound with the structure of the formula A-2 with iridium trichloride under the protection of inert gas, and after the reaction is finished, cooling, precipitating, washing and drying to obtain the compound with the structure of the formula B-2;
y2, under the protection of inert gas, reacting the compound with the structure of the formula B-2 with silver trifluoromethanesulfonate and methanol, and after the reaction is finished, cooling, carrying out column chromatography and concentrating to obtain the compound with the structure of the formula C-2;
y3, under the protection of inert gas, carrying out reflux reaction on the compound with the structure of the formula C-2 and the compound with the structure of the formula D-2 in absolute ethyl alcohol for 20-24h, and after the reaction is finished, carrying out suction filtration, alcohol washing, drying, column chromatography and concentration to obtain the compound with the structure of the formula II;
the synthetic route for the compound of formula II is as follows:
when m is 0 and n is 3, the structure of formula 1 is shown as formula III, and the specific synthesis steps of formula III are as follows:
k1, reacting the compound with the structure of the formula A-3 with iridium trichloride under the protection of inert gas, and after the reaction is finished, cooling, precipitating, washing and drying to obtain the compound with the structure of the formula B-3;
k2, under the protection of inert gas, reacting the compound with the structure of the formula B-3 with silver trifluoromethanesulfonate and methanol, and after the reaction is finished, cooling, carrying out column chromatography and concentrating to obtain the compound with the structure of the formula C-3;
k3, under the protection of inert gas, carrying out reflux reaction on the compound with the structure of the formula C-3 and the compound with the structure of the formula D-3 in absolute ethyl alcohol for 20-24h, and after the reaction is finished, carrying out suction filtration, alcohol washing, drying, column chromatography and concentration to obtain the compound with the structure of the formula III;
the synthetic route for the compound of formula III is as follows:
9. application of the iridium metal complex luminescent material as claimed in any one of claims 1 to 7, wherein the iridium metal complex luminescent material is applied to an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer, the organic layer being located between the first electrode and the second electrode, and at least one of the organic layers comprising the iridium metal complex light-emitting material as claimed in any one of claims 1 to 7; the iridium metal complex luminescent material exists in the organic layer in a single form or mixed with other substances.
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| CN112645987A (en) * | 2020-12-27 | 2021-04-13 | 浙江华显光电科技有限公司 | Iridium metal complex and organic photoelectric element using same |
| CN112679552A (en) * | 2020-12-27 | 2021-04-20 | 浙江华显光电科技有限公司 | Iridium metal complex and organic photoelectric element using same |
| JP2023009002A (en) * | 2021-07-02 | 2023-01-19 | 北京夏禾科技有限公司 | Organic electroluminescent material and device thereof |
| US11952390B2 (en) | 2020-06-20 | 2024-04-09 | Beijing Summer Sprout Technology Co., Ltd. | Phosphorescent organic metal complex and use thereof |
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