CN114621196A - Organic light-emitting material, preparation method thereof and organic electroluminescent device - Google Patents
Organic light-emitting material, preparation method thereof and organic electroluminescent device Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 41
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 48
- 239000010410 layer Substances 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 19
- 238000010992 reflux Methods 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 14
- 238000002386 leaching Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 6
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 235000019441 ethanol Nutrition 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
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- 230000008569 process Effects 0.000 abstract description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 239000007788 liquid Substances 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- 239000012065 filter cake Substances 0.000 description 24
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- 239000000741 silica gel Substances 0.000 description 23
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- 238000009987 spinning Methods 0.000 description 15
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- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
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- 239000004698 Polyethylene Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 238000000967 suction filtration Methods 0.000 description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000008213 purified water Substances 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000011521 glass Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
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- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- -1 1-phenylisoquinolinyl Chemical group 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000007874 V-70 Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1011—Condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
Abstract
The invention discloses an organic luminescent material, a preparation method thereof and an organic electroluminescent device. According to the organic luminescent material with the novel structure, the specific macrocyclic structure is selected, the obtained organic compound is used for an organic electroluminescent device, the starting voltage of the device is reduced, the luminous efficiency of the device is improved, the service life of the device is prolonged, the preparation method of the organic luminescent material is simple in process, and the prepared product is high in purity.
Description
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to an organic light-emitting material, a preparation method thereof and an organic electroluminescent device.
Background
The OLED device serving as a novel display technology has the unique advantages of self-luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, can be applied to flat panel displays and new generation illumination, and can also be used as a backlight source of an LCD.
Since the first report of high efficiency organic light emitting diodes, the industry has been working on how to improve the efficiency and stability of the devices. The phosphorescent material has strong spin-orbit coupling effect, and can simultaneously utilize singlet excitons and triplet excitons, so that the quantum efficiency in the phosphorescent electroluminescent device theoretically reaches 100 percent. However, the phosphorescent material has a long excited-state lifetime, and triplet-triplet annihilation and triplet-polaron annihilation are easily formed when the triplet exciton concentration is high, resulting in a serious decrease in efficiency. Therefore, phosphorescent materials are often incorporated as guests into host materials to reduce the self-concentration quenching process. It is important to select a suitable host material in Phosphorescent organic electroluminescent devices (Ph OLEDs). For example, a host material with a wide band gap may cause an increase in the turn-on voltage of the phosphorescent organic electroluminescent device, and accordingly, high efficiency may be obtained. The appropriate host material is selected, and then the host-guest doping mode is adopted to adjust the light color, the brightness and the efficiency, so that the purpose of improving the performance of the organic electroluminescent display device can be achieved. In general, the requisite properties of the host material include: (1) the high triplet state energy level is possessed; (2) the carrier mobility is better and can be matched with the energy level of the adjacent layer; (3) has high thermal stability and film forming stability.
At present, OLED display and illumination are widely commercialized and applied, the photoelectric requirement of a client terminal on an OLED screen body is continuously improved, and in order to meet the requirements, in addition to the lean refinement in the OLED panel manufacturing process, the development of OLED materials capable of meeting higher device indexes is very important. Therefore, the development of stable and efficient host materials can reduce the driving voltage, improve the luminous efficiency and the service life of the device, and have important practical application value.
Disclosure of Invention
In view of the above, the present invention provides an organic light emitting material, a method for preparing the same, and an organic electroluminescent device. According to the organic luminescent material with the novel structure, the specific macrocyclic structure is selected, so that the obtained organic compound is used for an organic electroluminescent device, the starting voltage of the device is reduced, the luminous efficiency of the device is improved, and the service life of the device is prolonged.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic light-emitting material has a structure shown in formula I:
wherein L is selected from one of a bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group;
ring Y1, ring Y2, ring Y3, and ring Y4 are each independently selected from a benzene ring;
Ar1has the following structure:
wherein the content of the first and second substances,
is a connection location;
R1and R2Are identical to or different from each other, and R1And R2Each independently selected from one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group, substituted or unsubstituted C10-C30 condensed ring group, and substituted or unsubstituted C5-C30 spiro ring.
Preferably, the formula I includes the following structure:
another object of the present invention is to provide a method for preparing the above organic light emitting material, wherein the synthetic route is as follows:
wherein X and Y are respectively and independently selected from halogen, specifically one of F, Cl, Br and I, and the other definitions are consistent with the requirements of formula I;
the specific synthesis steps are as follows:
(1) under the protection of nitrogen, uniformly mixing a compound shown in the formula IV, a compound shown in the formula V, anhydrous potassium carbonate, toluene, anhydrous ethanol and water, adding palladium tetratriphenylphosphine, carrying out reflux reaction at 100 ℃, obtaining a reaction solution after the reaction is finished, cooling to room temperature, and carrying out chromatography, concentration, leaching and drying to obtain an intermediate compound shown in the formula III;
(2) under the protection of nitrogen, uniformly mixing a compound shown in a formula II, a compound shown in a formula III, toluene and sodium tert-butoxide, sequentially adding tris (dibenzylideneacetone) dipalladium and 50% of tri-tert-butylphosphine by volume fraction, carrying out reflux reaction at 110 ℃, obtaining a reaction solution after the reaction is finished, cooling to room temperature, carrying out chromatography, concentration, leaching and drying, and obtaining a final product shown in a formula I.
Preferably, the molar ratio of the compound of formula IV, the compound of formula V, anhydrous potassium carbonate and tetratriphenylphosphine palladium in step (1) is 1: (2.0-3.0): (2.5-3.5): (0.01-0.03).
Preferably, the volume ratio of the compound of the formula V to the toluene in the step (1) is 1g (8-12 mL); the volume ratio of the toluene to the absolute ethyl alcohol to the water is 2:1: 1; the reflux reaction time is 12-30 hours.
Preferably, in step (2), the molar ratio of the compound of formula II, the compound of formula III, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and the 50% volume fraction of tri-tert-butylphosphine is 1: (1.1-1.6): (2.5-3.5): (0.02-0.04): (0.04-0.08).
Preferably, the mass-to-volume ratio of the compound of the formula II to the toluene in the step (2) is 1g (8-12mL), and the reflux reaction time is 16-24 hours.
An organic electroluminescent device comprising an anode, a cathode and a plurality of organic layers deposited between the anode and the cathode, and wherein at least one of the organic layers comprises the organic light-emitting material of claim 1 or 2.
Preferably, the organic layer includes a hole injection layer, an electron transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, and the light emitting layer includes the organic light emitting material according to claim 1 or 2.
The invention also aims to provide the application of the organic electroluminescent device in an organic luminescent device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
Through the technical scheme, compared with the prior art, the invention has the following beneficial effects:
the novel OLED material provided by the invention takes a polycyclic structure compound as a matrix, and obtains a novel OLED material which has a high triplet state energy level, a good carrier mobility, high thermal stability and high film forming stability, and can be matched with an adjacent energy level by introducing a specific group into the matrix structure and adjusting the position of a substituent. The material can be applied to the field of organic electroluminescence, is used as a main material of a light-emitting layer, can reduce driving voltage, and improves the light-emitting efficiency and the service life of a device.
The preparation method of the organic luminescent material provided by the invention is simple in process, and the prepared product is high in purity.
Detailed Description
The technical solutions in the embodiments of the present invention are 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 formula I-1 is prepared, and the specific synthetic steps are as follows:
weighing the formula IV-1 (40mmol,13.00g), the formula V-1 (100 mmol 1,23.98g) and potassium carbonate (120mmol,16.56g) into a reaction system under the protection of nitrogen, adding 130mL of toluene, 65mL of absolute ethyl alcohol and 65mL of purified water, and adding a catalyst Pd (PPh) under the protection of nitrogen3)4(0.40mmol,0.46g) refluxing for 24 hours, then cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g silica gel, spinning the organic phase filtrate until no liquid flows out, adding 100ml dichloromethane for dissolving, carrying out column chromatography on the solution (200-300 meshes, 400g), developing agent DCM (PE) ═ 2:1, spinning the receiving solution until no liquid flows out, adding petroleum ether, stirring for 20min, carrying out suction filtration, leaching the filter cake with petroleum ether, drying the filter cake in vacuum,intermediate compound III-1 (10.47g, 83% yield) was obtained in an HPLC purity of greater than 99%.
Mass spectrum calculated 315.38; the test value was 315.65.
Weighing formula II-1 (20mmol,7.77g), formula III-1 (24 mmol 1,7.57g) and sodium tert-butoxide (60mmol,5.76g) in a nitrogen protection system, adding 77.7ml toluene, and adding Pd as a catalyst in the nitrogen protection system2(dba)3(0.6mmol,0.55g) and P (t-Bu)3(1.2mmol, 0.24g), refluxing at 110 ℃ for 22h under the protection of nitrogen, cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g of silica gel, spinning the organic phase filtrate until no liquid flows out, adding 100ml of dichloromethane for dissolving, performing column chromatography on the solution (200-300 meshes, 400g) with a developing agent DCM (PE: 3: 1), spinning the received liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula I-1 (7.22g, 58% yield) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 622.73; the test value was 622.59.
Elemental analysis calculated as C: 86.79; h is 4.21; n:9.00. test value C: 86.78; h is 4.20; and N is 9.02.
Example 2
The preparation of the compound of formula I-29 comprises the following steps:
weighing IV-29 (40mmol,13.00g), V-29 (100 mmol 1,23.98g) and potassium carbonate (120mmol,16.56g) into a reaction system under the protection of nitrogen, adding 130mL of toluene, 65mL of absolute ethyl alcohol and 65mL of purified water, and adding a catalyst Pd (PPh) under the protection of nitrogen3)4(0.40mmol,0.46g) refluxing for 24 hours, cooling to 25 deg.C, passing the organic phase through a silica gel funnel of 200g silica gel, rotating the organic phase filtrate until no liquid flows out, adding 100ml dichloromethane to dissolve, performing column chromatography on the solution (200-300 mesh, 400g), developing agent DCM: PE: 2:1, rotating the receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20min, filtering the filter cake with stone, and filtering the filter cakeThe oil ether is used for elution, and the filter cake is dried in vacuum to obtain the intermediate compound III-29 (10.47g, the yield is 83 percent), the HPLC purity of which is more than 99 percent.
Mass spectrum calculated 315.38; the test value was 315.65.
Weighing the formula II-29 (20mmol,11.44g), the formula III-29 (22 mmol 1,6.94g) and sodium tert-butoxide (50mmol,4.81g) into a reaction system under the protection of nitrogen, adding 137ml toluene and Pd as a catalyst under the protection of nitrogen2(dba)3(0.37mmol,0.55g) and P (t-Bu)3(0.8mmol, 0.16g), refluxing at 110 ℃ for 24h under the protection of nitrogen, cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g of silica gel, spinning the organic phase filtrate until no liquid flows out, adding 120ml of dichloromethane for dissolving, performing column chromatography on the solution (200-300 meshes, 400g) with a developing agent DCM (PE: 3: 1), spinning the received liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula I-29 (10.89g, the yield is 64%) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 851.03; the test value was 851.24.
Elemental analysis calculated as C: 88.92; h is 4.50; n is 6.58, and the test value is 88.91; h is 4.53; and N is 6.56.
Example 3
The preparation of the compound of formula I-70 comprises the following steps:
weighing IV-70 (40mmol,13.00g), V-70 (100 mmol 1,23.98g) and potassium carbonate (120mmol,16.56g) into a reaction system under the protection of nitrogen, adding 130mL of toluene, 65mL of absolute ethyl alcohol and 65mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.40mmol,0.46g) refluxing for 24 hours, cooling to 25 deg.C, passing the organic phase through a silica gel funnel of 200g silica gel, swirling the organic phase filtrate until no liquid flows out, adding 100ml dichloromethane to dissolve, performing column chromatography on the solution (200-300 mesh, 400g), developing solvent DCM: PE: 2:1, swirling the receiving solution until no liquid flows out, addingAdding petroleum ether, stirring for 20min, vacuum filtering, eluting the filter cake with petroleum ether, and vacuum drying the filter cake to obtain intermediate compound III-70 (10.47g, 83% yield), with HPLC purity of more than 99%.
Mass spectrum calculated 315.38; the test value was 315.65.
Weighing II-70 (20mmol,13.41g), III-70 (30mmo1,9.46g) and sodium tert-butoxide (60mmol,5.76g) in a nitrogen protection system, adding 140ml toluene, and adding Pd as a catalyst in nitrogen protection2(dba)3(0.8mmol,0.73g) and P (t-Bu)3(1.6mmol, 0.32g), refluxing at 110 ℃ for 24h under the protection of nitrogen, cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g of silica gel, spinning the organic phase filtrate until no liquid flows out, adding 150ml of dichloromethane for dissolving, performing column chromatography on the solution (200-300 meshes, 400g) with a developing agent DCM (PE: 3: 1), spinning the received liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula I-70 (7.06g, 39% yield) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 905.12; the test value was 905.34.
Elemental analysis, calculated value C is 88.91; h is 4.90; n:6.19, test value C: 88.92; h is 4.88; and N is 6.20.
Example 4
The preparation of the compound of formula I-107 is carried out by the following steps:
weighing the formula IV-107 (40mmol,13.00g), the formula V-107 (100 mmol 1,23.98g) and potassium carbonate (120mmol,16.56g) into a reaction system under the protection of nitrogen, adding 130mL of toluene, 65mL of absolute ethyl alcohol and 65mL of purified water, and adding a catalyst Pd (PPh) under the protection of nitrogen3)4(0.40mmol,0.46g) under reflux for 24h, then cooling to 25 deg.C, passing the organic phase through a silica gel funnel of 200g silica gel, swirling the organic phase filtrate until no liquid flows out, adding 100ml dichloromethane to dissolve, subjecting the solution to column chromatography (200-300 mesh, 400g), developing solvent DCM: PEAnd (2: 1), spinning the receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching a filter cake with the petroleum ether, and drying the filter cake in vacuum to obtain an intermediate compound III-107 (10.47g, the yield is 83%) with the HPLC purity of more than 99%.
Mass spectrum calculated 315.38; the test value was 315.65.
Weighing II-107 (20mmol,9.92g), III-107 (26 mmol 1,8.20g) and sodium tert-butoxide (60mmol,5.76g) in a nitrogen protection system, adding 100ml toluene, and adding Pd as a catalyst in the nitrogen protection2(dba)3(0.6mmol,0.55g) and P (t-Bu)3(1.2mmol, 0.24g), refluxing at 110 ℃ for 24h under the protection of nitrogen, cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g of silica gel, spinning the organic phase filtrate until no liquid flows out, adding 100ml of dichloromethane for dissolving, performing column chromatography on the solution (200-300 meshes, 400g) with a developing agent DCM (PE: 3: 1), spinning the received liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula I-107 (7.28g, 47% yield) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 774.93; the test value was 774.80.
Elemental analysis calculated as C: 88.35; h is 4.42; n is 7.23, and the test value is C is 88.32; h is 4.44; and N is 7.24.
Example 5
The preparation of the compound of formula I-140 comprises the following steps:
weighing IV-140 (40mmol,13.00g), V-140 (100 mmol 1,23.98g) and potassium carbonate (120mmol,16.56g) into a reaction system under the protection of nitrogen, adding 130mL of toluene, 65mL of absolute ethyl alcohol and 65mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.40mmol,0.46g) was refluxed for 24 hours, then cooled to 25 ℃ and the organic phase was passed through a silica funnel of 200g silica gel, the organic phase filtrate was swirled until no liquid flowed out, 100ml dichloromethane was added to dissolve it and the solution was dissolvedPerforming liquid column chromatography (200-300 meshes, 400g), using a developing agent DCM: PE: 2:1, rotating the receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain an intermediate compound III-140 (10.47g, the yield is 83%) with the HPLC purity of more than 99%.
Mass spectrum calculated 315.38; the test value was 315.65.
Weighing the formula II-140 (20mmol,11.40g), the formula III-140 (28 mmol 1,8.83g) and the sodium tert-butoxide (56mmol,5.38g) into a reaction system under the protection of nitrogen, adding 120ml toluene and Pd as a catalyst under the protection of nitrogen2(dba)3(0.6mmol,0.55g) and P (t-Bu)3(1.2mmol, 0.24g), refluxing at 110 ℃ for 24h under the protection of nitrogen, cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g of silica gel, spinning the organic phase filtrate until no liquid flows out, adding 100ml of dichloromethane for dissolving, performing column chromatography on the solution (200-300 meshes, 400g) with a developing agent DCM (PE: 3: 1), spinning the received liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound I-140 (10.53g, the yield is 62%) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 849.01; the test value was 849.25.
Elemental analysis calculated as C: 89.13; h is 4.27; n is 6.60, and the test value is C is 89.10; h is 4.28; and N is 6.62.
Example 6
The preparation of the compound of formula I-160 comprises the following steps:
weighing IV-160 (40mmol,13.00g), V-160 (100 mmol 1,23.98g) and potassium carbonate (120mmol,16.56g) into a reaction system under the protection of nitrogen, adding 130mL of toluene, 65mL of absolute ethyl alcohol and 65mL of purified water, and adding catalyst Pd (PPh) under the protection of nitrogen3)4(0.40mmol,0.46g) was refluxed for 24 hours, then cooled to 25 ℃ and the organic phase was passed through a silica gel funnel with 200g silica gel and the organic phase filtrate was spun freeAnd (3) allowing the liquid to flow out, adding 100ml of dichloromethane for dissolution, carrying out column chromatography on the solution (200-300 meshes, 400g), carrying out developing agent DCM (polyethylene glycol) 2:1, rotating the receiving liquid until no liquid flows out, adding petroleum ether, stirring for 20min, carrying out suction filtration, leaching a filter cake with the petroleum ether, and drying the filter cake in vacuum to obtain an intermediate compound III-160 (10.47g, the yield is 83%) with the HPLC purity of more than 99%.
Mass spectrum calculated 315.38; the test value was 315.65.
Weighing the compounds of the formulas II-160 (20mmol,9.29g), III-160 (24 mmol 1,7.57g) and sodium tert-butoxide (60mmol,5.77g) into a reaction system under the protection of nitrogen, adding 100ml toluene and Pd as a catalyst under the protection of nitrogen2(dba)3(0.4mmol,0.37g) and P (t-Bu)3(0.8mmol, 0.16g), refluxing at 110 ℃ for 24h under the protection of nitrogen, cooling to 25 ℃, passing the organic phase through a silica gel funnel of 200g of silica gel, spinning the organic phase filtrate until no liquid flows out, adding 100ml of dichloromethane for dissolving, performing column chromatography on the solution (200-300 meshes, 400g) with a developing agent DCM (PE: 3: 1), spinning the received liquid until no liquid flows out, adding petroleum ether, stirring for 20min, performing suction filtration, leaching the filter cake with petroleum ether, and drying the filter cake in vacuum to obtain the compound of formula I-160 (5.45g, 39% yield) with the HPLC purity of more than 99.5%.
Mass spectrum calculated 698.83; the test value was 698.51.
Elemental analysis, calculated C is 87.66; h is 4.33; n is 8.02, and the test value is C is 87.66; h is 4.30; and N is 8.05.
The synthesis methods of other compounds are the same as those described above, which are not repeated herein, and the mass spectrum or molecular formula of other synthesis examples is shown in table 1 below:
table 1:
the present invention also provides an organic electroluminescent device made of the organic luminescent material, more particularly, the organic luminescent material of chemical formula 1.
In order to further describe the present invention, the following more specific examples are set forth
Example 17
Device fabrication
The ITO glass substrate with the coating thickness of 150nm is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30 minutes, the ITO glass substrate is repeatedly cleaned for 2 times by the distilled water, the ultrasonic cleaning is carried out for 10 minutes, after the cleaning by the distilled water is finished, solvents such as isopropanol, acetone, methanol and the like are sequentially subjected to ultrasonic cleaning and then dried, the ITO glass substrate is transferred into a plasma cleaning machine, the ITO glass substrate is cleaned for 5 minutes, and the ITO glass substrate is sent into an evaporation machine. Firstly, a compound 2-TNATA is evaporated on an ITO (anode) in vacuum to form a hole injection layer with the thickness of 55 nm; evaporating a compound NPB on the hole injection layer in vacuum to form a hole transport layer with the thickness of 35nm, wherein the evaporation rate is 0.1 nm/s; forming an electroluminescent layer on the hole transport layer, and specifically operating as follows: the compound host material of the present invention of formula 1-1 as a light emitting layer was placed in a cell of a vacuum vapor deposition apparatus, and Ir (piq) as a dopant was added2(acac) [ bis- (1-phenylisoquinolinyl) acetylacetonatoiridium (III)]Placing in another chamber of a vacuum vapor deposition apparatus, evaporating two materials at different rates simultaneously, Ir (piq)2The acac concentration is 6%, and the total film thickness of evaporation plating is 40 nm; depositing Bphen on the luminescent layer by vacuum evaporation to form an electron transport layer with the thickness of 20nm, wherein the evaporation rate is 0.1 nm/s; LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is vacuum-evaporated on the electron injection layer to be used as a cathode of the device.
Wherein the compound 2-TNATA, NPB, Ir (piq)2The structural formulas of acac and Bphen are shown below.
With reference to the procedure of example 17 above, except that the host material of formula I-1 was replaced with the host materials of formula I-19, formula I-29, formula I-32, formula I-47, formula I-52, formula I-61, formula I-70, formula I-88, formula I-94, formula I-107, formula I-115, formula I-130, formula I-140, formula I-160, and formula I-167, respectively, to prepare organic electroluminescent devices of the corresponding compounds.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 17, except that 4,4' -bis (9-carbazole) biphenyl (C1) was used in place of the compound of the formula I-1 in example 17.
Comparative example 2
An organic electroluminescent device was produced in the same manner as in example 17, except that 4,4' -bis (9-carbazole) biphenyl (C2) was used in place of the compound of the formula I-1 in example 17.
The organic electroluminescent devices obtained in the device examples 17 to 31 and the device comparative examples 1 and 2 were characterized at a luminance of 2000(nits), and the test results were as follows:
table 2:
as can be seen from table 2, the organic electroluminescent devices prepared using the compounds provided by the present invention as host materials of the light emitting layer have significantly reduced driving voltage, significantly improved luminous efficiency, power efficiency and lifetime, as compared to the organic electroluminescent devices prepared using the comparative compounds C1 and C2 as host materials.
The above examples only show the effect data of formula 1-1, formula I-19, formula I-29, formula I-32, formula I-47, formula I-52, formula I-61, formula I-70, formula I-88, formula I-94, formula I-107, formula I-115, formula I-130, formula I-140, formula I-160, formula I-167, which are representative sampling tests, and the overall data is not very different from experimental data, and can represent the effect of other unrecited structures.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed in the embodiment corresponds to the method disclosed in the embodiment, so that the description is simple, and the relevant points can be referred to the description of the method part.
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 organic light-emitting material is characterized in that the structure is shown as formula I:
wherein L is selected from one of a bond, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group;
ring Y1, ring Y2, ring Y3, and ring Y4 are each independently selected from a benzene ring;
Ar1has the following structure:
wherein the content of the first and second substances,
is a connection position;
R1and R2Are identical to or different from each other, and R1And R2Each independently selected from one of hydrogen, deuterium, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 6-to 30-membered aromatic heterocyclic group, substituted or unsubstituted C10-C30 condensed ring group, and substituted or unsubstituted C5-C30 spiro ring.
2. The organic light-emitting material of claim 1, wherein the formula I comprises the following structure:
3. the method for preparing an organic light-emitting material according to claim 1 or 2, wherein the synthetic route is as follows:
wherein X and Y are each independently selected from halogen;
the specific synthesis steps are as follows:
(1) under the protection of nitrogen, uniformly mixing a compound shown in the formula IV, a compound shown in the formula V, anhydrous potassium carbonate, toluene, anhydrous ethanol and water, adding palladium tetratriphenylphosphine, carrying out reflux reaction at 100 ℃, obtaining a reaction solution after the reaction is finished, cooling to room temperature, and carrying out chromatography, concentration, leaching and drying to obtain an intermediate compound shown in the formula III;
(2) under the protection of nitrogen, uniformly mixing a compound shown in a formula II, a compound shown in a formula III, toluene and sodium tert-butoxide, sequentially adding tris (dibenzylideneacetone) dipalladium and 50% tri-tert-butylphosphine, carrying out reflux reaction at 110 ℃, obtaining a reaction solution after the reaction is finished, cooling to room temperature, and carrying out chromatography, concentration, leaching and drying to obtain a final product shown in a formula I.
4. The method according to claim 3, wherein the molar ratio of the compound of formula IV, the compound of formula V, anhydrous potassium carbonate and palladium tetratriphenylphosphine in step (1) is 1: (2.0-3.0): (2.5-3.5): (0.01-0.03).
5. The method according to claim 3, wherein the volume ratio of the compound of formula V to toluene in step (1) is 1g (8-12 mL); the volume ratio of the toluene to the absolute ethyl alcohol to the water is 2:1: 1; the reflux reaction time is 12-30 hours.
6. The method according to claim 3, wherein the molar ratio of the compound of formula II, the compound of formula III, sodium tert-butoxide, tris (dibenzylideneacetone) dipalladium and the 50% tri-tert-butylphosphine in step (2) is 1: (1.1-1.6): (2.5-3.5): (0.02-0.04): (0.04-0.08).
7. The method according to claim 3, wherein the mass-to-volume ratio of the compound of formula II to toluene in step (2) is 1g (8-12mL), and the reflux reaction time is 16-24 hours.
8. An organic electroluminescent device comprising an anode, a cathode, and a plurality of organic layers disposed between the anode and the cathode, wherein at least one of the organic layers comprises the organic light-emitting material of claim 1 or 2.
9. An organic electroluminescent device according to claim 8, wherein the organic layer comprises a hole injection layer, an electron transport layer, a light emitting layer, an electron transport layer and an electron injection layer, and the light emitting layer comprises the organic light emitting material according to claim 1 or 2.
10. Use of an organic electroluminescent device as claimed in claim 8 or 9 in an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
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| CN111170974A (en) * | 2019-12-31 | 2020-05-19 | 浙江华显光电科技有限公司 | Host compound and electroluminescent device using same |
| KR20210034528A (en) * | 2019-09-20 | 2021-03-30 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| WO2021073393A1 (en) * | 2019-10-18 | 2021-04-22 | 广州华睿光电材料有限公司 | Phosphorescent host material and application thereof |
| CN112979548A (en) * | 2019-12-17 | 2021-06-18 | 北京鼎材科技有限公司 | Compound and application thereof |
| CN113454186A (en) * | 2019-02-25 | 2021-09-28 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN114394928A (en) * | 2022-01-12 | 2022-04-26 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
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| CN113454186A (en) * | 2019-02-25 | 2021-09-28 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
| KR20210034528A (en) * | 2019-09-20 | 2021-03-30 | 주식회사 엘지화학 | Novel compound and organic light emitting device comprising the same |
| WO2021073393A1 (en) * | 2019-10-18 | 2021-04-22 | 广州华睿光电材料有限公司 | Phosphorescent host material and application thereof |
| CN112979548A (en) * | 2019-12-17 | 2021-06-18 | 北京鼎材科技有限公司 | Compound and application thereof |
| CN111170974A (en) * | 2019-12-31 | 2020-05-19 | 浙江华显光电科技有限公司 | Host compound and electroluminescent device using same |
| CN114394928A (en) * | 2022-01-12 | 2022-04-26 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound, preparation method thereof and organic electroluminescent device |
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