CN112209973A - O-containing organic electrophosphorescent material and application thereof - Google Patents
O-containing organic electrophosphorescent material and application thereof Download PDFInfo
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Abstract
The invention relates to the technical field of organic electroluminescent display, and particularly discloses a novel O-containing organic electrophosphorescent material and application thereof in an organic electroluminescent device. The O-containing organic electrophosphorescent material provided by the invention has a structure shown as a general formula (I). The organic electrophosphorescent material is applied to an organic electroluminescent device, and the prepared electroluminescent device has the superior performances of high purity, high brightness and high efficiency.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent display, and particularly discloses a novel O-containing organic electrophosphorescent material and application thereof in organic electroluminescent devices (OLEDs).
Background
Electroluminescent display devices can be classified into inorganic electroluminescent display devices and organic electroluminescent display devices according to the difference in the material constituting the light emitting layer. Organic electroluminescent display devices have incomparable advantages over inorganic electroluminescent display devices, such as full-color luminescence in the visible spectrum, extremely high brightness, extremely low driving voltage, fast response time, and simple manufacturing processes.
The research of organic electroluminescence starts in the 60 th 19 th century, Pope realizes electroluminescence on anthracene single crystal for the first time, but the driving voltage reaches 100V at that time, and the quantum efficiency is very low. In 1987, Tang and VanSlyke used a double-layer thin film structure in which 8-hydroxyquinoline aluminum complex (Alq3) was used as a light-emitting layer and an electron-transporting layer, and TAPC was used as a hole-transporting layer, and an ITO electrode and an Mg: Ag electrode were used as an anode and a cathode, respectively, to produce high luminance (>1000cd/m2) The driving voltage of the green organic electroluminescent thin-film device with high efficiency (1.5lm/W) is reduced to below 10V. In 1990, polymer thin film electroluminescent devices made from poly (p-phenylene vinylene) (PPV) by Burroughes et al gave blue-green light output with quantum efficiency of 0.05% and driving voltage of less than 14V. In 1991, Braun et al produced green and orange light outputs with quantum efficiencies of 1% using derivatives of PPV, with drive voltages of about 3V. These research advances have immediately attracted considerable attention from scientists of various countries, and research on organic electroluminescence has been widely conducted worldwide and has gradually started to move to the market.
In general, an organic electroluminescent display device has a structure including an anode formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode sequentially formed on the anode. The hole transport layer, the light emitting layer, and the electron transport layer are organic thin films composed of organic compounds. The driving principle of the organic electroluminescent display device having the above-described structure is as follows: holes are injected from the anode into the light-emitting layer through the hole transport layer as long as a voltage is applied between the anode and the cathode; at the same time, electrons are injected from the cathode into the light-emitting layer through the electron transport layer; in the light emitting layer region, carriers are rearranged to form excitons, and the excited excitons are shifted to the ground state, causing light emission from the light emitting layer molecules.
Light emitting materials are classified into two groups according to a light emitting mechanism, one group being fluorescent materials using singlet excitons, and the other group being phosphorescent materials using triplet excitons. The phosphorescent material has higher luminous efficiency than the fluorescent material because the phosphorescent material can utilize 75% of triplet excitons and 25% of singlet excitons, whereas the fluorescent material utilizes only 25% of singlet excitons. The phosphorescent material is generally an organometallic compound containing a heavy metal, and forms a light emitting layer composed of a host material and a dopant material that emits light by transferring energy from the host material.
At present, organometallic complexes having phosphorescent emission and organic electroluminescent devices are reported, and various organometallic complex phosphorescent materials are also disclosed in the patent. For example, US patent No. 6687266 discloses iridium (Ir) complexes containing benzimidazole ligands, which have hindered the possibility of commercialization due to serious problems of low phosphorescence efficiency, poor stability and lifetime. Therefore, it would be of great significance to structurally improve such compounds to develop new phosphorescent light-emitting materials with better performance and promote commercial application.
Disclosure of Invention
The invention aims to develop a novel O-containing organic electrophosphorescent luminescent material so as to improve the phosphorescence quantum efficiency and the electroluminescent efficiency of the material and improve the stability of the material and the service life of a device.
Specifically, in a first aspect, the present invention provides an O-containing organic electrophosphorescent material having a structure represented by general formula (i):
wherein:
R1～R11independently selected from hydrogen atom, deuterium atom, alkyl, deuterated alkyl, alkoxy, alkylamino, alkylthio, halogen atom, trifluoromethyl, alicyclic hydrocarbon group, aromatic group and heterocyclic aromatic group, and/or R1～R11Wherein adjacent substituents form a fused ring structure by bridging;
l is a monovalent bidentate anionic ligand wherein the linking atoms X, Y are each independently selected from the group consisting of an oxygen atom, a nitrogen atom, a carbon atom;
n is 1, 2 or 3.
As a preferred embodiment of the present invention, L is phenylpyridyl, substituted phenylpyridyl, acetylacetonate or substituted acetylacetonate.
Further preferably, L is a group of formula L1 or formula L2:
wherein:
in the formula L1, R12～R19Independently selected from hydrogen atom, deuterium atom, alkyl, deuterated alkyl, alkoxy, alkylamino, alkylthio, halogen atom, trifluoromethyl, alicyclic hydrocarbon group, aromatic group and heterocyclic aromatic group, and/or R12～R19Wherein adjacent substituents form a fused ring structure by bridging.
In the formula L2, R20～R26Independently selected from hydrogen atom, deuterium atom, alkyl, deuterated alkyl, alkoxy, alkylamino, alkylthio, halogen atom, trifluoromethyl, alicyclic hydrocarbon group, aromatic group and heterocyclic aromatic group, and/or R20～R26Wherein adjacent substituents form a fused ring structure by bridging.
More preferably, L is arbitrarily selected from the following groups:
as a preferred embodiment of the present invention, the phosphorescent material is a compound represented by formula I or formula II or formula III:
wherein m is 1 or 2.
R in general formula I, general formula II and general formula III1～R26As previously defined.
As a preferred embodiment of the present invention, said R1～R11Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C20The alicyclic hydrocarbon group, halogen atom, alkoxy group containing 1-5C atoms, alkylamino group containing 1-5C atoms, alkylthio group containing 1-5C atoms, trifluoromethyl group, phenyl group, substituted phenyl group, heterocyclic aromatic group; and/or, R1～R11Wherein adjacent substituents form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted five-membered ring, a substituted or unsubstituted six-membered ring, a substituted or unsubstituted five-membered heterocyclic ring and a substituted or unsubstituted six-membered heterocyclic ring, and the substituent used for substitution is a halogen atom and C1～C5Straight-chain or branched alkyl, phenyl, deuterated C1～C5The straight chain or branched chain-containing alkyl, the benzo group, the substituted phenyl and the substituted benzo group, wherein at least one heteroatom contained in the five-membered heterocyclic ring or the six-membered heterocyclic ring is selected from an oxygen atom and a sulfur atom.
As a preferred embodiment of the present invention, said R12～R19Independently selected from hydrogen atom and deuteriumAtom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C20The alicyclic hydrocarbon group, halogen atom, alkoxy group containing 1-5C atoms, alkylamino group containing 1-5C atoms, alkylthio group containing 1-5C atoms, trifluoromethyl group, phenyl group, substituted phenyl group, heterocyclic aromatic group; and/or, R12～R19Wherein adjacent substituents form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted five-membered ring, a substituted or unsubstituted six-membered ring, a substituted or unsubstituted five-membered heterocyclic ring and a substituted or unsubstituted six-membered heterocyclic ring, and the substituent adopted for substitution is C1～C5Linear or branched alkyl, deuterated C1～C5The alkyl, the halogen atom, the phenyl, the substituted phenyl, the benzo, the substituted benzo, the pyrido and the substituted pyrido of the straight chain or the branched chain, the five-membered heterocyclic ring or the six-membered heterocyclic ring contains at least one heteroatom, and the heteroatom is selected from oxygen atom and sulfur atom.
As a preferred embodiment of the present invention, said R20～R26Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5The linear or branched alkyl group of (1), (1) to (5) carbon atoms, a halogen atom, an alkoxy group, an alkylamino group, an alkylthio group and a trifluoromethyl group.
Wherein, C1～C5The straight-chain or branched alkyl group of (2) may be a methyl group, an ethyl group, a propyl group (e.g., n-propyl group, isopropyl group), a butyl group (e.g., n-butyl group, isobutyl group, sec-butyl group, tert-butyl group), a pentyl group (e.g., n-pentyl group, neopentyl group) or the like.
Deuterated C1～C5The straight-chain or branched alkyl group of (1) means an alkyl group in which a part of hydrogen atoms is substituted by deuterium, and may be, for example, deuterated methyl, deuterated isopropyl, deuterated pentyl, deuterated neopentyl, deuterated butyl (e.g., deuterated n-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated tert-butyl), etc.
Alkoxy containing 1 to 5C atoms is CnH2n+1O-, wherein n is 1 to 5. The alkoxy group having 1 to 5C atoms may be a methoxy group, an ethoxy group or the like.
The halogen atom is fluorine atom, bromine atom, etc.
The substituted phenyl group includes alkyl-substituted phenyl groups, deuterated alkyl-substituted phenyl groups, halogen atom-substituted phenyl groups, and the like.
R1～R11The adjacent substituents in (b) may also form a fused-ring structure by bridging, and when the fused-ring structure is formed, the fused-ring structure may be any one of a substituted or unsubstituted five-membered ring, a substituted or unsubstituted six-membered ring, a substituted or unsubstituted five-membered heterocyclic ring, and a substituted or unsubstituted six-membered heterocyclic ring. At least one heteroatom is contained in the five-membered heterocyclic ring or the six-membered heterocyclic ring, and the heteroatom is selected from oxygen atom, sulfur atom and nitrogen atom. For example, the fused ring structure may be a benzo ring, a furo ring, a thieno ring, or the like. The fused ring structure may be further substituted with a substituent, for example, with a benzo group, with an alkyl-substituted benzo group (e.g., methyl-substituted benzo group, ethyl-substituted benzo group, propyl-substituted benzo group), with a deuterated alkyl-substituted benzo group (e.g., deuterated methyl-substituted benzo group, deuterated propyl-substituted benzo group), etc.
As a further preferred embodiment of the present invention, said R1～R11Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C12The alicyclic hydrocarbon group of (1), a halogen atom, a phenyl group, a pyridyl group, a substituted phenyl group, a substituted pyridyl group; and/or, R1～R11Wherein adjacent substituent groups form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted benzene ring and a substituted or unsubstituted five-membered heterocycle, and the substituent group adopted by the substitution is a halogen atom and C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, benzoThe five-membered heterocyclic ring contains at least one heteroatom, and the heteroatom is selected from oxygen atom and sulfur atom.
More preferably, said R1～R11Each independently selected from a hydrogen atom, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an adamantyl group, a cyclohexyl group, a cyclooctyl group, a deuterated methyl group, a deuterated ethyl group, a phenyl group, a fluorine atom, and a bromine atom; and/or, R1～R11Wherein adjacent substituents form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted benzene ring, a substituted or unsubstituted furan ring and a substituted or unsubstituted thiophene ring, and the substituent adopted for substitution is a benzo group.
As a further preferred embodiment of the present invention, said R12～R19Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C12The alicyclic hydrocarbon group of (1), a halogen atom, a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group; and/or, R12～R19Wherein adjacent substituent groups form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted six-membered ring and a substituted or unsubstituted five-membered heterocycle, and the substituent group adopted by the substitution is a halogen atom and C1～C5Linear or branched alkyl, deuterated C1～C5The straight-chain or branched-chain alkyl, the benzo group, the substituted benzo group, the phenyl group, the substituted phenyl group, the pyrido group and the substituted pyrido group, the five-membered heterocyclic ring contains at least one heteroatom, and the heteroatom is optionally selected from an oxygen atom and a sulfur atom.
More preferably, said R12～R19Independently selected from hydrogen atom, fluorine atom, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, sec-butyl, isobutyl, adamantyl, deuterated methyl, phenyl, substituted phenyl (such as tolyl, xylyl, monofluorophenyl, bromophenyl, difluorophenyl)Radicals, etc.); and/or, R12～R19Wherein the adjacent substituents form a fused ring structure by bridging, the fused ring structure is a substituted or unsubstituted six-membered ring, a substituted or unsubstituted five-membered heterocyclic ring, and the substituents used for substitution are a bromine atom, a fluorine atom, a phenyl group, a methyl group, an ethyl group, a n-propyl group, an isopropyl group, a n-butyl group, a tert-butyl group, a sec-butyl group, an isobutyl group, a pyrido group, a substituted pyrido group (e.g., a methyl-substituted pyrido group, a deuterated methyl-substituted pyrido group), and the like. The five-membered heterocyclic ring contains at least one heteroatom, and the heteroatom is optionally selected from an oxygen atom and a sulfur atom.
As a further preferred embodiment of the present invention, said R20～R26Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5A straight or branched alkyl group, a halogen atom.
More preferably, said R20～R26Each independently selected from hydrogen atom, methyl group and ethyl group.
As a preferred embodiment of the invention, the O-containing organic electrophosphorescent material is selected from compounds represented by the following structural formula:
in the research, the iridium-containing complex containing benzimidazole structural units as main ligands is found to be shown as the following formula,
the purity of the material is obviously reduced in the sublimation process, which indicates that the material is not suitable for preparing an OLED panel by the evaporation technology at present. Theoretical analysis and experiment prove that the instability of the material comes from an N-C bond formed by an N atom on benzimidazole in a ligand and a group connected with the N atom, and a weaker C-N bond is prone to be subjected to fracture decomposition at high temperature to cause purity reduction. Through a large number of experiments, we find that two benzene rings are connected by an oxygen atom to form a ring structure, namely the ring structure is changed into a parent nucleus structure shown as the following:
the probability of degradation of the molecules is greatly reduced by the entropy effect. Meanwhile, the introduction of a ring structure is found to effectively improve the rigidity of the ligand and weaken the excited state nonradiative transition mechanism, so that the effect of improving the phosphorescence quantum efficiency of the iridium-containing phosphorescent material supported by the ligand is achieved.
The invention provides a novel organic electrophosphorescent material, which is a novel O-containing benzimidazole ligand-supported phosphorescent material with a ring structure, namely an iridium-containing material supported by a cyclized benzimidazole structural unit ligand. The phosphorescent material provided by the invention can effectively solve the problems of low phosphorescent efficiency, poor stability and short service life of the conventional phosphorescent material, improves the phosphorescent quantum efficiency and electroluminescent efficiency of the material, and improves the stability of the material and the service life of devices. The electroluminescent device prepared by the phosphorescent material has the advantages of high purity, high brightness and high efficiency. The material can be used as green phosphorescent luminescent material.
Specifically, the novel organic electrophosphorescent material provided by the invention is a phosphorescent material supported by a benzimidazole ligand with a cyclic structure, and compared with an iridium-containing compound formed by an acyclic benzimidazole ligand, the iridium-containing complex formed by the cyclic benzimidazole ligand has the following advantages:
(1) according to the complex, two aromatic groups on the benzimidazole ligand form a ring, so that the tendency of high-temperature thermal decomposition of phosphorescent molecules caused by the existence of a weaker C-N bond can be reduced, the thermal stability of the material is improved, the phenomenon of purity reduction in the sublimation or evaporation process is reduced, and the commercialization of the material is possible;
(2) the stability of the material is improved, so that the stability of an OLED device using the material is improved, and the service life is prolonged;
(3) the complex increases the rigidity of ligand molecules due to cyclization, weakens the non-radiative transition mechanism of the excited state of phosphorescent molecules, thereby improving the phosphorescent quantum efficiency of the material, showing that the luminous efficiency on a device is improved, and bringing positive effects for reducing the power consumption of an OLED screen body.
The novel iridium-containing material supported by the cyclized benzimidazole structural unit ligand provided by the invention is used as a luminescent layer luminescent material of an organic electroluminescent device, can improve the phosphorescence quantum efficiency and electroluminescent efficiency of the material, and improves the stability of the material and the service life of the device.
In a second aspect, the invention provides the application of the organic electrophosphorescent material in the preparation of organic electroluminescent devices.
Preferably, the organic electrophosphorescent material is used as a dye material of a host material in an organic electroluminescent device. The material of the invention can be used as a dye doped in an organic electroluminescent device to emit light, and the electroluminescent device prepared by the phosphorescent material of the invention has the advantages of high purity, high brightness and high efficiency.
Further preferably, the doping concentration of the phosphorescent material in the host material is 3-12%, more preferably 5-10%, and more preferably 6-8%. When the doping concentration of the phosphorescent light-emitting material in the host material is about 7%, the performance of the device is best. Wherein, the doping concentration is mass percentage concentration.
In a third aspect, the present invention provides an organic electroluminescent device comprising a light-emitting layer comprising the phosphorescent material provided by the present invention.
Preferably, the light emitting layer includes a host material and a dye material, and the dye material includes the phosphorescent material provided by the present invention.
Further preferably, the doping concentration of the phosphorescent material in the host material is 3-12%, more preferably 5-10%, more preferably 6-8%, and more preferably 7%.
Specifically, the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of light-emitting unit layers and a cathode layer which are sequentially formed on the substrate; the light-emitting unit layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and a plurality of light-emitting layers are arranged between the hole transport layer and the electron transport layer. The luminescent material of the luminescent layer is the iridium-containing phosphorescent material provided by the invention.
In a fourth aspect, the invention further provides a display device comprising the organic electroluminescent device.
In a fifth aspect, the invention further provides a lighting device comprising the organic electroluminescent device.
Detailed Description
The technical solution of the present invention will be described in detail by specific examples. The following examples are intended to illustrate the present invention, but are not intended to limit the scope of the present invention, and other equivalent changes or modifications made without departing from the spirit of the present invention are intended to be included within the scope of the appended claims.
Example 1: synthesis of ligand P1
The synthetic route is as follows:
the specific experimental steps are as follows:
(1) adding 2-fluoronitrobenzene (14.1g, 0.1mol) and 2-bromoaniline (25.7g, 0.15mol) into a 2L three-neck flask with mechanical stirring, raising the temperature to 180 ℃, keeping the temperature and reacting for more than 30 hours under the protection of argon, wherein the color gradually turns into red in the reaction process, and finally gradually turns into deep red. After the reaction was completed, the organic phase was separated, extracted, dried, column-chromatographed, and the solvent was spin-dried to obtain 24.8g of M1 as an orange-red solid with a yield of 85%.
(2) In a 1L three-necked flask equipped with a mechanical stirrer, M1(29.2g, 0.1mol), sodium sulfide nonahydrate (96g, 0.4mol), ethanol (200mL), water (100mL) and nitrogen were added, and the mixture was heated to reflux and refluxed for 3 hours to complete the reaction. The organic phase was separated, extracted, dried, column chromatographed, and the solvent dried to give 22.8g of white solid M2 with 87% yield.
(3) In a 1L three-necked flask equipped with a mechanical stirrer, M2(26.2g, 0.1mol) and 300mL of acetone were added to be completely dissolved, a solution of KOH (11.2g,0.2mol) dissolved in water (50mL) was added, o-bromobenzoyl chloride (22g, 0.1mol) was slowly dropped into the flask, a solid was gradually precipitated from the flask, and after the dropping, the reaction was carried out at room temperature for 2 hours to complete the reaction. After neutralization, the organic phase was separated, extracted, dried, column chromatographed, and the solvent was dried to give M3 as a white solid (33.9 g) in 76% yield.
(4) Adding M3(44.6g, 0.1mol) into a 1L three-necked flask, adding 200mL of glycol ether under the protection of nitrogen, gradually heating to reflux, gradually dissolving the solid, magnetically stirring, keeping the temperature and reacting for 3 hours, and finishing the reaction. The organic phase was separated, extracted, dried, column chromatographed and the solvent dried to give 34.7g of M4 as a pale pink solid in 81% yield.
(5) Under the protection of nitrogen, M4(42.8g, 0.1mol) and 800mL of anhydrous THF are added into a 2L three-necked bottle, the mixture is cooled to-78 ℃,2.5M n-hexane solution of n-butyllithium (100mL, 0.25mol) is slowly dripped under stirring, the dripping time is about 30mins, 50mL of anhydrous THF is used for flushing a dropping funnel after dripping, and the reaction solution of M5 is obtained after 1.5 hours of heat preservation after dripping. Subsequently, 200mL of diethylene glycol dimethyl ether and P-toluenesulfonic acid monohydrate (50g, 0.26mol) were added, heated to 150 ℃ and stirred to react for 5 hours until TLC detection of the disappearance of the raw materials, the reaction system was cooled, 200mL of saturated saline solution and 200mL of dichloromethane were added to extract three times, the organic phases were combined, dried over anhydrous magnesium sulfate, the solvent was dried by spinning, and column chromatography was performed to obtain 26.6g of intermediate P1 as a white solid with a yield of 58%.
Product MS (m/e): 284.09, respectively; elemental analysis (C)19H12N2O): theoretical value C: 80.25%, H: 4.22%, N: 9.85 percent; found value C: 80.32%, H: 4.36%, N: 9.73 percent.
Example 2: synthesis of ligand P2
Referring to the synthetic procedure of example 1, except for replacing o-bromobenzoyl chloride with 2-bromo-4-methylbenzoyl chloride in step (3), the other starting materials and procedures were the same as in example 1 to obtain ligand P2.
Product MS (m/e): 298.11, respectively; elemental analysis (C)20H14N2O): theoretical value C: 80.52%, H: 4.73%, N: 9.39 percent; found value C: 80.67%, H: 4.87%, N: 9.23 percent.
Example 3: synthesis of ligand P3
Referring to the synthetic procedure of example 1, except for replacing 2-bromoaniline with 2-bromo-4-methylaniline in step (1), the other starting materials and procedures were the same as in example 1 to obtain ligand P3.
Product MS (m/e): 298.11, respectively; elemental analysis (C)20H14N2O): theoretical value C: 80.52%, H: 4.73%, N: 9.39 percent; found value C: 80.67%, H: 4.85%, N: 9.21 percent.
Example 4: synthesis of ligand P4
Referring to the synthetic procedure of example 1, except for replacing 2-fluoronitrobenzene with 2-fluoro-5-isopropylnitrobenzene in step (1), the other starting materials and procedures were the same as in example 1, to obtain ligand P4.
Product MS (m/e): 326.14, respectively; elemental analysis (C)22H18N2O): theoretical value C: 80.96%, H: 5.56%, N: 8.58 percent; found value C: 80.64%, H: 5.72%, N: 8.73 percent.
Example 5: synthesis of ligand P5
Referring to the synthetic procedure of example 1, except that 4-bromo-dibenzofuran-3-carbonyl chloride was used in place of o-bromobenzoyl chloride in step (3), the other starting materials and procedures were the same as in example 1 to give ligand P5.
Product MS (m/e): 374.11, respectively; elemental analysis (C)25H14N2O2): theoretical value C: 80.2%, H: 3.77%, N: 7.48 percent; found value C: 80.44%, H: 3.82%, N: 7.36 percent.
Example 6: synthesis of ligand P6
The specific experimental steps are as follows: in a 500mL three-necked flask equipped with mechanical stirring, the system was made inert by three cycles of vacuum-nitrogen filling so that the system was under inert atmosphere, ligand P3(29.83g, 0.1mol), DMSO-D6(340g, 4.04mol), potassium tert-butoxide (1.12g, 10mmol) were added, the temperature was raised to 120 ℃ under nitrogen protection, the reaction was stirred well for 10 hours, the reaction system was cooled to room temperature, a large amount of deionized water was added, extraction was carried out three times with 300mL of ethyl acetate, the organic phases were combined, washed twice with saturated saline, the organic phase was separated, extracted, dried, column-chromatographed, and the solvent was spin-dried to give 27.12g of P6 as a white solid with a yield of 90%, and nuclear magnetic deuterium substitution of 97.5% was confirmed.
Example 7: synthesis of Compound I-49
The reaction formula is as follows:
the specific experimental steps are as follows:
(1) phenylpyridine (15mmol,2.5mL), iridium trichloride hydrate (6mmol,2.01 g), ethylene glycol monoethyl ether (45 mL) and distilled water (15 mL) were sequentially added to a 100mL three-necked flask equipped with a mechanical stirring, reflux condenser and nitrogen protection device. Vacuumizing and filling N2Repeating the steps for five times to remove oxygen in the system. Heated to 110 ℃ under reflux for 24 hours. After natural cooling, 10mL of distilled water is added, and the mixture is shaken, filtered, washed with water and washed with ethanol. Drying in vacuo afforded 2.6 g of crude M7 as a yellow solid in 81.0% yield.
(2) In a 500mL three-necked flask equipped with a nitrogen blanket, dichloro-bridged intermediate M7(10.7 g, 10mmol) was sequentially added, 150mL of dichloromethane was added, and the mixture was sufficiently stirred, then 200mL of a methanol solution of silver trifluoromethanesulfonate (6.4 g, 25mmol) was added, and the mixture was stirred for 24 hours in the dark, and after cooling to room temperature, the generated AgCl was filtered off with celite, and the filtrate was dried by spinning to obtain a yellowish solid powder. The solid was used in the next reaction without further treatment.
(3) The solid yellowish brown (5.1 g, 6.9mmol) obtained in step (2) and ligand P1(6 g, 21mmol) were added to a 250ml three-necked flask, 100ml of ethanol was then added, the mixture was heated under reflux for 36 hours, the reaction was cooled to room temperature, the resultant yellow solid was filtered, and the solid was dissolved in dichloromethane and separated by column chromatography to give 10.24 g of a yellow solid with a yield of 61.1%.
Product MS (m/e): 784; elemental analysis (C)41H27IrN4O): theoretical value C: 62.76%, H: 3.44%, N: 7.14 percent; found value C: 62.57%, H: 3.63%, N: 7.12 percent.
Example 8: synthesis of Compound II-1
The reaction formula is as follows:
the specific experimental steps are as follows:
(1) a500 mL three-neck flask equipped with a mechanical stirring device, a reflux condenser and a nitrogen protection device was charged with ligand P1(25mmol,7.11 g), iridium trichloride hydrate (10mmol,3.35 g), 90mL of ethylene glycol monoethyl ether and 30mL of distilled water in this order. Vacuumizing and filling N2Repeating the steps for 5 times to remove oxygen in the system. Heated to 110 ℃ and refluxed for 24 hours. After natural cooling, 10mL of distilled water is added, and the mixture is shaken, filtered, washed with water and washed with ethanol. Drying in vacuo afforded 6.35 g of crude M6 as a yellow solid in 64.0% yield.
(2) To a 250mL three-necked flask equipped with a magnetic stirring and reflux condenser, the above intermediate M6(5mmol, 7.94 g), acetylacetone (25mmol, 2.5 g, 2.6mL), and anhydrous Na were added in this order2CO3(22mmol, 2.35 g)) And ethylene glycol monoethyl ether 100 mL. Vacuumizing and filling N2Repeating the steps for 5 times to remove oxygen in the system. N is a radical of2Heated to reflux for 24 hours in an oil bath at 120 ℃ under protection. Naturally cooling to room temperature, filtering, washing with water, n-hexane and diethyl ether in sequence, and drying to obtain a yellow crude product. By CH2Cl2Column separation after dissolution, eluent CH2Cl2Washing and solvent suction drying gave 7.4 g of yellow powder in 86.2% yield.
Product MS (m/e): 858; elemental analysis (C)43H29IrN4O4): theoretical value C: 60.13%, H: 3.38%, N: 6.53 percent; found value C: 60.25%, H: 3.44%, N: 6.39 percent.
Example 9: synthesis of Compound III-1
The reaction formula is as follows:
the specific experimental steps are as follows: into a 250ml three-necked flask equipped with a magnetic stirring and reflux condenser, Ir (acac)3(10mmol, 4.9 g), ligand P1(40mmol, 11.37 g), glycerol 150 mL. Vacuumizing and filling N2Repeating the steps for 5 times to remove oxygen in the system. N is a radical of2The mixture was heated to reflux in an oil bath at 190 ℃ for 24 hours under protection. Naturally cooling to room temperature, filtering, washing with water, n-hexane and diethyl ether in sequence, and drying to obtain a yellow crude product. By CH2Cl2Column separation after dissolution, eluent CH2Cl2Washing and solvent suction drying gave 5.7g of a yellow solid in 41% yield.
Product MS (m/e): 1042; elemental analysis (C)57H33IrN6O3): theoretical value C: 65.64%, H: 3.17%, N: 8.06 percent; found value C: 65.92%, H: 3.35%, N: 7.96 percent.
Other specific phosphorescent compounds listed in the present invention were synthesized with reference to the above synthesis method.
Example 10: stability verification experiment
5 g of the known control GD01 and the compound II-1 obtained according to the invention, respectively, were placed in a high vacuum sublimation apparatus at 6.0 x 10-4Sublimation was carried out at 310 ℃ under a vacuum of pascal for 20 hours, and the sublimation results are shown in table 1.
TABLE 1
As can be seen from the data in the table above, the purity of the compound II-1 provided by the invention is unchanged after sublimation, while the purity of the compound GD01 is obviously reduced after sublimation. Therefore, the cyclization strategy adopted by the invention can effectively improve the thermal stability of the prepared phosphorescent material.
Example 11: preparation of OLED device
The application embodiment of the OLED device of the compound provided by the invention is as follows, the embodiment provides a group of OLED green light devices, and the structure of the device is as follows: ITO/HATCN (1nm)/HT01(60nm)/TAPC (40nm)/DIC-TRZ: 5% phosphorescent material compound of the present invention (40nm)/TPBI (5nm) ET01: QLi (1:1) (30nm)/LiF (1 nm)/Al.
The molecular structure of each functional layer material is as follows:
preparing an OLED-1 device:
the compound II-1 prepared by the invention is selected as a phosphorescent material, the doping concentration of the compound II-1 is 5%, and an OLED device is prepared by the following specific preparation method:
(1) carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing the glass plate in deionized water, ultrasonically removing oil in an acetone-ethanol mixed solvent (the volume ratio is 1:1), baking the glass plate in a clean environment until the water is completely removed, cleaning the glass plate by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
(2) placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, carrying out vacuum evaporation on the anode layer film to form HATCN as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 1 nm; then, evaporating a first hole layer HT01 at the evaporation rate of 0.1nm/s and the thickness of 60 nm; then evaporating a second hole transport layer TAPC (tantalum polycarbonate), wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 40 nm;
(3) the EML is evaporated on the hole transport layer in vacuum and used as a light emitting layer of the device, the EML comprises a main material DIC-TRZ and a dye material II-1 of the invention, the doping concentration is 5%, an organic light emitting layer of the device is formed, the evaporation rate is 0.2nm/s, and the total film thickness of the evaporation is 40 nm; then 5nm of TPBI is evaporated to form a hole blocking layer, and the evaporation rate is 0.1 nm/s;
(4) then evaporating ET01: QLi with the mass ratio of 1:1 on the hole blocking layer as an electron transport material of an electron transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30 nm;
(5) LiF with the thickness of 1nm is sequentially subjected to vacuum evaporation on the electron transport layer to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device. And packaging to obtain the OLED-1 device.
Preparing OLED-2-OLED-3 devices:
according to the preparation method of the OLED-1 device, the OLED-2 and OLED-3 devices are prepared by changing the doping concentration of the dye material II-1 in the host material DIC-TRZ in the step (3) from 5% to 7% and 10%, respectively.
The performance of the devices OLED-1 to OLED-3 prepared above was tested, and the results of testing the performance of each device are detailed in Table 2.
TABLE 2
Comparing the detection results of the three light emitting devices, it can be seen that the performance of the light emitting device OLED-2 is the best, that is, when the doping concentration is about 7%, the brightness is the highest, and the efficiency is also the highest.
Preparing OLED-4-OLED-10 devices:
according to the preparation method of the OLED-1 device, the dye material II-1 in the step (3) is respectively replaced by the compounds I-1, I-49, I-51, II-3, III-1, III-2 and III-4, and the doping concentration in the host material DIC-TRZ is 7%, so that OLED-4-OLED-10 devices are prepared.
Comparative device 1 was prepared using compound GD01 of known structure as a dye material instead of dye material II-1 in the OLED-1 device, and the doping concentration in the host material DIC-TRZ was 7%.
The performance of the devices OLED-2, OLED-4-OLED-10 and the comparative devices are tested, and the performance test results of the devices are shown in Table 3.
TABLE 3
From the above results, it can be seen that, compared with GD01, II-1, the luminous efficiency of the corresponding device is improved and the lifetime is significantly prolonged due to the improved stability of the compound itself, and the compounds with different ligand modes: on one hand, the colors of the emitted light can be adjusted, the photoelectric properties of the corresponding devices and the service lives of the devices are also obviously influenced, the light emitting properties of the compound and the wide adjustability of device data are shown, and solutions can be provided according to different customer requirements. Therefore, the phosphorescent material provided by the invention can effectively solve the problems of the commonly used phosphorescent material in the aspects of color purity, luminous efficiency, service life and the like, and an organic electroluminescent device prepared by using the phosphorescent material provided by the invention has excellent performances of high purity, high brightness and high efficiency.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. An O-containing organic electrophosphorescent material is characterized by having a structure shown as a general formula (I):
wherein:
R1～R11independently selected from hydrogen atom, deuterium atom, alkyl, deuterated alkyl, alkoxy, alkylamino, alkylthio, halogen atom, trifluoromethyl, alicyclic hydrocarbon group, aromatic group and heterocyclic aromatic group, and/or R1～R11Wherein adjacent substituents form a fused ring structure by bridging;
l is a monovalent bidentate anionic ligand wherein the linking atoms X, Y are each independently selected from the group consisting of an oxygen atom, a nitrogen atom, a carbon atom;
n is 1, 2 or 3.
2. The phosphorescent material of claim 1, wherein L is phenylpyridyl, substituted phenylpyridyl, acetylacetonate, or substituted acetylacetonate;
preferably, L is a group of formula L1 or formula L2:
wherein:
in the formula L1, R12～R19Independently selected from hydrogen atom, deuterium atom, alkyl, deuterated alkyl, alkoxy, alkylamino, alkylthio, halogen atom, trifluoromethyl, alicyclic hydrocarbon group, aromatic group and heterocyclic aromatic group, and/or R12～R19Wherein adjacent substituents form a fused ring structure by bridging; alternatively, the first and second electrodes may be,
in the formula L2, R20～R26Independently selected from hydrogen atom, deuterium atom, alkyl, deuterated alkyl, alkoxy, alkylamino, alkylthio, halogen atom, trifluoromethyl, alicyclic hydrocarbon group, aromatic group and heterocyclic aromatic group, and/or R20～R26Wherein adjacent substituents form a fused ring structure by bridging.
3. The phosphorescent material of claim 2, wherein the phosphorescent material is a compound of formula I or formula II or formula III:
wherein m is 1 or 2.
4. Phosphorescent material according to claim 2 or 3, characterized in that R is1～R11Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C20The alicyclic hydrocarbon group, halogen atom, alkoxy group containing 1-5C atoms, alkylamino group containing 1-5C atoms, alkylthio group containing 1-5C atoms, trifluoromethyl group, phenyl group, substituted phenyl group, heterocyclic aromatic group; and/or, R1～R11Wherein adjacent substituents form a fused ring structure through bridging, and the fused ring structure is a substituted or unsubstituted five-membered ring, a substitutedOr any one of unsubstituted six-membered ring, substituted or unsubstituted five-membered heterocycle and substituted or unsubstituted six-membered heterocycle, wherein the substituent for substitution is halogen atom, C1～C5Straight-chain or branched alkyl, phenyl, deuterated C1～C5The straight chain or branched chain-containing alkyl, the benzo group, the substituted phenyl and the substituted benzo group, wherein at least one heteroatom contained in the five-membered heterocycle or the six-membered heterocycle is selected from oxygen atom and sulfur atom; and/or the presence of a gas in the gas,
the R is12～R19Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C20The alicyclic hydrocarbon group, halogen atom, alkoxy group containing 1-5C atoms, alkylamino group containing 1-5C atoms, alkylthio group containing 1-5C atoms, trifluoromethyl group, phenyl group, substituted phenyl group, heterocyclic aromatic group; and/or, R12～R19Wherein adjacent substituents form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted five-membered ring, a substituted or unsubstituted six-membered ring, a substituted or unsubstituted five-membered heterocyclic ring and a substituted or unsubstituted six-membered heterocyclic ring, and the substituent adopted for substitution is C1～C5Linear or branched alkyl, deuterated C1～C5The straight chain or branched chain-containing alkyl, halogen atom, phenyl, substituted phenyl, benzo, substituted benzo, pyrido and substituted pyrido of the five-membered heterocycle or the six-membered heterocycle, wherein the heteroatom is at least one and is optionally selected from oxygen atom and sulfur atom; and/or the presence of a gas in the gas,
the R is20～R26Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5The linear or branched alkyl group of (1), (1) to (5) carbon atoms, a halogen atom, an alkoxy group, an alkylamino group, an alkylthio group and a trifluoromethyl group.
5. The phosphorescent material of claim 4, wherein R is1～R11Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C12The alicyclic hydrocarbon group of (1), a halogen atom, a phenyl group, a pyridyl group, a substituted phenyl group, a substituted pyridyl group; and/or, R1～R11Wherein adjacent substituent groups form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted benzene ring and a substituted or unsubstituted five-membered heterocycle, and the substituent group adopted by the substitution is a halogen atom and C1～C5Linear or branched alkyl, deuterated C1～C5The straight-chain or branched-chain-containing alkyl, the benzo group and the substituted benzo group of (1), wherein the five-membered heterocyclic ring contains at least one heteroatom which is optionally selected from oxygen atom and sulfur atom; and/or the presence of a gas in the gas,
the R is12～R19Each independently selected from hydrogen atom, deuterium atom, C1～C5Linear or branched alkyl, deuterated C1～C5Linear or branched alkyl, C3～C12The alicyclic hydrocarbon group of (1), a halogen atom, a phenyl group, a substituted phenyl group, a pyridyl group, a substituted pyridyl group; and/or, R12～R19Wherein adjacent substituent groups form a fused ring structure through bridging, the fused ring structure is any one of a substituted or unsubstituted six-membered ring and a substituted or unsubstituted five-membered heterocycle, and the substituent group adopted by the substitution is a halogen atom and C1～C5Linear or branched alkyl, deuterated C1～C5The straight-chain or branched-chain alkyl, the benzo group, the substituted benzo group, the phenyl group, the substituted phenyl group, the pyrido group and the substituted pyrido group of the (C) compound have at least one heteroatom, and the heteroatom is optionally selected from oxygen atom and sulfur atom; and/or the presence of a gas in the gas,
the R is20～R26Each independently selected from hydrogen atom, deuterium atom, C1～C5A linear or branched alkyl group of,Deuterated C1～C5A straight or branched alkyl group, a halogen atom.
6. The phosphorescent material of any one of claims 1 to 5, wherein the phosphorescent material is any selected from compounds represented by the following structural formulae:
7. use of the phosphorescent material of any one of claims 1 to 6 in the preparation of an organic electroluminescent device;
preferably, the phosphorescent material is used as a light-emitting material in an organic electroluminescent device;
further preferably, the doping concentration of the phosphorescent material in the host material is 3-12%, more preferably 5-10%, more preferably 6-8%, and more preferably 7%.
8. An organic electroluminescent device comprising a light-emitting layer comprising the phosphorescent material according to any one of claims 1 to 6;
preferably, the light emitting layer comprises a host material and a dye material, the dye material comprising the phosphorescent material according to any one of claims 1 to 6;
further preferably, the doping concentration of the phosphorescent material in the host material is 3-12%, more preferably 5-10%, more preferably 6-8%, and more preferably 7%.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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