CN108264486B - Novel imidazole compound, preparation thereof and electroluminescent device - Google Patents
Novel imidazole compound, preparation thereof and electroluminescent device Download PDFInfo
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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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Abstract
The invention provides a novel imidazole derivative, wherein an anthracene structure is introduced into an imidazole compound and is connected with R1、R2And R3The groups improve the three-dimensional performance of the compound, the performance can be improved by adjusting the molecular weight and the types of ligands, and the like, and a device prepared by using the novel imidazole derivative has the characteristics of high brightness, excellent heat resistance, long service life, high efficiency and the like.
Description
Technical Field
The present invention relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. In particular, it relates to novel imidazole compounds as electroluminescent materials and their use as an organic electroluminescent device.
Background
A general Organic Light Emitting Device (OLED) is composed of a cathode, an anode, and organic layers interposed between the cathode and the anode, and the device is composed of a transparent ITO anode, a hole injection layer (TIL), a Hole Transport Layer (HTL), a light emitting layer (EL, a Hole Blocking Layer (HBL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), a LiAl, and the like, and 1 to 2 organic layers may be omitted as needed, a voltage is formed between two electrodes of the device, holes are injected from the cathode electron injection side to the anode side, electrons and holes are recombined in the light emitting layer to form an excited state, and when the excited state returns to a stable ground state, fluorescent molecules of the light emitting layer emit light, the light emitting material is classified into a fluorescent material and a phosphorescent material, the light emitting layer is formed by doping a phosphorescent material (organic metal) in the fluorescent host material and doping a fluorescent (organic matter containing nitrogen) dopant in the fluorescent host material and by using a dopant (DCM, rubrene, DCJTB, etc.) have been developed as a method for achieving a long wavelength, and the factors of emission wavelength, efficiency, driving voltage, lifetime, etc. are improved by such doping. The material for forming the luminescent layer generally has centrosomes such as benzene, naphthalene, fluorene, spirobifluorene, anthracene, pyrene, carbazole and the like and ligands such as benzene, biphenyl, naphthalene, heterocycle and the like; the combination positions of para position, meta position and ortho position, and the substitution structures of cyano, fluorine, methyl, tertiary butyl and the like.
The present OLED panels are becoming larger, and more delicate and colorful materials are needed, wherein the key point for the solution is blue materials, especially high performance materials that shift from light blue to dark blue, and on the other hand, high glass transition temperature materials that have good color coordinates of the emission wavelength, low driving voltage, high efficiency light emission efficiency and good thermal stability are needed.
The aromatic heterocyclic compound such as oxadiazole, thiadiazole, pyrimidine and the like can be used as a material for forming an electron transport layer, the material for the electron transport layer needs to have better thermal stability, higher electron mobility, high efficiency of a luminous body and long service life, and the novel imidazole derivative provided by the invention has better performance than the similar material at the present stage.
Disclosure of Invention
The invention provides a novel imidazole derivative, wherein an anthracene structure is introduced into an imidazole compound, the stereo performance of the compound is improved by connecting Ar1 groups, and the performance can be improved by adjusting the molecular weights of ligands R1 and R2 and the types of the ligands.
The technical scheme of the invention is as follows, and the structural general formula of the novel imidazole derivative is shown in chemical formula 1:
r1, R2 and R3 represent the same or different groups, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C60 heterocyclic group, substituted or unsubstituted C6-C60 arylamine; the substituted groups are hydrogen, halogen, C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamine, C1-C60 alkylmercapto, C6-C60 arylmercapto, C2-C60 alkylene, C2-C60 alkyne, C3-C60 cycloalkyl, C6-C60 aryl, C8-C60 aralkenyl, silicon base and C5-C60 heterocyclic group.
Preferably, R1, R2 and R3 may be the same or different groups selected from the group consisting of novel imidazole compounds specified by any one of the following formulae:
wherein X and Y may be the same or different, hydrogen atom, halogen, cyano, C1-C30 alkyl, C1-C30 alkoxy, C2-30 alkenyl, C7-30 aralkyl, C7-30 aralkyloxy, C6-30 aryl, C6-30 aryloxy, C5-30 heterocycle, C6-30 aromatic amine.
Preferably, the R1, R2 and R3 are independently selected from phenyl, 1-naphthyl, pyrenyl, pyridyl, triarylamine, carbazolyl, biphenyl, quinolyl and substituted carbazolyl; the substituents are selected from phenyl.
Preferably, the compound has a structure shown as 001-017:
the present application also provides a method of preparing a compound according to the above scheme, comprising:
carrying out a coupling reaction on a compound with a structure shown in a formula (A) and a compound with a structure shown in a formula (B) to generate a novel imidazole derivative shown in a chemical formula 1;
x is Cl, Br, I;
wherein, the compound of formula (A) is obtained by NBS bromination reaction of formula (C);
wherein the compound of formula (C) is obtained by the cyclization reaction of formula (E) and formula (F);
wherein, R1, R2 and R3 are the same or different, substituted or non-substituted C1-C60 alkyl, substituted or non-substituted C6-C60 aryl, substituted or non-substituted C5-C60 heterocyclic radical, substituted or non-substituted C7-C60 condensed ring radical, substituted or non-substituted C6-C60 arylamine radical; the substituted group comprises any one of hydrogen, halogen, C1-C60 alkyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamine, C1-C60 alkylmercapto, C6-C60 arylmercapto, C2-C60 alkylene, C2-C60 alkyne, C3-C60 cycloalkyl, C6-C60 aryl, C8-C60 aralkenyl, silicon base and C5-C60 heterocycle.
The application also provides application of the compound in the scheme or the compound prepared by the preparation method in the scheme as a luminescent material in preparing an organic electroluminescent device.
The invention provides a new imidazole derivative, wherein an anthracene structure is introduced into an imidazole compound, and the performance can be improved by improving the stereo performance of the compound, adjusting the molecular weights of ligands R1, R2 and R3 and the types of the ligands, and the like.
It is another aspect of the present invention to provide a fabricated organic electroluminescent device comprising the novel imidazole derivatives of the above chemical formula 1. Comprising a first electrode, a second electrode and one or more organic compound layers disposed between said electrodes, characterized in that at least one organic compound layer comprises at least one novel imidazole based compound according to the invention.
The novel imidazole derivatives are included in the organic layer in a single form or in a mixed form with other substances.
The organic layer at least comprises any one of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport functions, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer having both electron transport and electron injection functions.
At least one of the hole injection layer, the hole transport layer, and the layer having both hole injection and hole transport functions is a conventional hole injection material, a hole transport material, a material having both hole injection and hole transport functions, or a material that can be generated from an electron transport material.
The term "organic layer" in this patent refers to all layers disposed between the first and second electrodes of the organic electronic device.
For example, the organic layer includes a light-emitting layer, the organic layer includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant, and includes an aromatic amine derivative in the light-emitting layer, i) the fluorescent host may be an aromatic amine derivative; ii) the fluorescent dopant may be an aromatic amine derivative; iii) the fluorescent host and the fluorescent dopant may be an aromatic amine derivative.
The light-emitting layer may be a red, yellow or cyan light-emitting layer. For example, the aromatic amine derivative for cyan in the light-emitting layer is used for cyan host or cyan dopant applications, and provides an organic light-emitting device having high efficiency, high luminance, high resolution, and long lifetime.
And the organic layer includes an electron transport layer including the novel imidazole derivative. Wherein the electron transport layer contains a metal-containing compound in addition to the novel imidazole derivative.
The organic layer includes a light-emitting layer and an electron-transporting layer, and the light-emitting layer and the electron-transporting layer each include the imidazole derivative (the light-emitting layer and the electron-transporting layer may include the new imidazole derivative, and may be the same or different).
The above organic electronic device is manufactured using the novel imidazole derivative of chemical formula 1 and conventional materials and methods for manufacturing the organic electronic device.
Another aspect of the present invention is that the above device may be used in an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), an electronic Paper (e-Paper), an Organic Photoreceptor (OPC), or an Organic Thin Film Transistor (OTFT). The organic light-emitting device is prepared by evaporating metal, conductive oxide and their alloy on the substrate by thin film evaporation, electron beam evaporation, physical vapor deposition, etc. to form anode, and evaporating cathode after the hole injection layer, hole transmission layer, light-emitting layer, hole blocking layer and electron transmission layer. The organic light emitting device is manufactured by sequentially evaporating the cathode material, the organic material layer and the anode material on the outer substrate.
The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, and an electron transport layer, and may be manufactured by using various solvent processes of a polymer material instead of a vapor deposition method, for example, a spin-coating method, a tape-casting method, a doctor-blading method, a Screen-Printing method, an ink-jet Printing method, a Thermal-Imaging method, or the like, to reduce the number of layers.
The organic device according to the present invention may also emit light from the front, from the back, or from both sides, depending on the materials used.
The compound of the present invention can be applied to organic devices such as organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, and organic transistors, and similar principles can be applied to organic light-emitting devices.
Detailed Description
The following will clearly and completely describe the technical solutions of the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All 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 Synthesis of intermediate M1
9-Anthranilic aldehyde (10.0g, 48.5mmol) and o-aminodiphenylamine (8.9g, 48.5mmol) were placed in dry DMF (100ml), sodium metabisulfite (11.0g, 58.2mmol) was added, reaction was carried out at 155 ℃ for 18h, after completion of the reaction, cooling to room temperature, washing with water, extraction with ethyl acetate, drying, evaporation of the solvent to dryness, and recrystallization from toluene gave intermediate M1(14.7g, y ═ 82%).
Example 2
Intermediates M2 to M5 were synthesized according to the above preparation method of intermediate M1, and Table 1 summarizes the reaction substances, the products and the yields in example 2 of the present invention.
Table 1 shows a summary of the reaction materials, the products and the yields in example 2 of the present invention
Example 3: synthesis of intermediate N1
Dissolving intermediate M1(14.7g, 39.6mmol) in dichloromethane (100ml), placing in an ice-water bath, adding NBS (7.0g, 39.6mol) for reaction for 2h, after the reaction is finished, washing with water, separating, drying an organic phase, evaporating a solvent to obtain a solid bromide, and separating and purifying by using a silica gel chromatography column to obtain intermediate N1(15.6g, y is 88%)
Example 4
Intermediates N2 to N5 were synthesized according to the above preparation method of intermediate N1, and Table 2 summarizes the reaction substances, the products and the yields in example 4 of the present invention.
TABLE 2 summary of reaction materials, formed materials and yields of example 4 of the present invention
Example 5: synthesis of Compound 001
Intermediate N1(15.6g, 34.7mmol), diphenylamine (6.4g, 38.1mmol) and sodium tert-butoxide (6.6g, 69.4mol) were added to a toluene solution (150ml), and the mixture was heated to reflux under nitrogen protection with the addition of a catalyst (0.2g, 0.3mmol) and a phosphorus ligand (0.1g, 0.6mmol) for 12 hours, after completion of the reaction, washed with water, the organic phase was separated, dried, concentrated, and purified by silica gel column chromatography to obtain compound (13.4g, y: 72%). Mass spectrum: 537.24.
example 6
Compounds 002-017 were synthesized according to the preparation method of the compound 001, and Table 3 summarizes the reaction substance, the production substance and the yield in example 6 of the present invention.
TABLE 3 summary of reaction materials, formed materials and yields of example 6 of the present invention
Example 7
The imidazole compounds 001, 005 and 017 prepared in the embodiments 5 to 6 of the invention are respectively prepared into the imidazole compounds with the concentration of 1 × 10- 6The luminous efficiency of the mol/L solution manufactured into a film by an Edinburdh-FL S920 device and a spin coating method is respectively tested, and the specific data are shown in the following table 4.
TABLE 4 luminous efficacy of the compounds prepared in examples 5 to 6
| Compound (I) | Luminous efficiency in dilute solution | Luminous efficiency in thin films |
| 001 | 93.6％ | 65.2％ |
| 005 | 94.7％ | 64.3％ |
| 017 | 93.8％ | 64.4％ |
As can be seen from the data in Table 4, the imidazole derivatives prepared in the examples of the present invention have a luminous efficiency of 94.03% in a dilute solution, and a luminous efficiency of 64.63% in a thin film. The imidazole derivatives provided by the invention have high luminous efficiency and can meet the requirements of OLED, and the materials are organic electroluminescent materials with excellent performance and are very promising organic electroluminescent materials.
Example 8
This example prepares a blue phosphorescent organic electroluminescent device as follows: cleaning of ITO (indium tin oxide) glass: respectively ultrasonically cleaning ITO glass by deionized water, acetone and ethanol for 15 minutes, and then treating the ITO glass in a plasma cleaner for 2 minutes; spin coating PEDOT on anode ITO glass: PSS is used as a hole injection layer, the rotating speed is 4000 revolutions per minute, annealing is carried out for 5 minutes at 200 ℃ in the air, then annealing is carried out for 15 minutes at 200 ℃ in nitrogen, and the thickness is 28 nm; in the PEDOT: the hole transport layer TCTA is evaporated on the PSS layer in vacuum, the speed is 0.5nm/min, and the thickness is 40 nm. On the hole transport layer TCTA, evaporating a luminescent layer MCP and FIrpic together, wherein the FIrpic accounts for 8% by mass, the total evaporation rate is 1.0nm/min, and the thickness is 10 nm; the electron transport layer compound is vacuum-evaporated on the light-emitting layer MCP & FIrpic by using the compounds 001, 005 and 017 shown in the preparation examples at the rate of 0.5nm/min and the thickness of 40 nm; evaporating LiF on the electron transport layer TPPB in vacuum at a rate of 0.5 nm; and evaporating cathode Al on LiF in vacuum with the thickness of 120 nm. The structure of the device is ITO/PEDOT: PSS (28nm)/TCTA (40 nm)/MCP: FIrpic 8% (10 nm)/Compound 001, 005, 017(40nm)/LiF (0.5nm)/Al (120 nm). Vacuum deposition was performed using an EL deposition apparatus manufactured by DOV corporation. The measurement was performed using a KEITHLEY gishili 235 type source measuring unit, a spectrascan pr650 spectral scanning colorimeter, to evaluate driving voltage, light emission luminance, light emission efficiency, light emission color, and the results are shown in table 5:
TABLE 5 partial data for devices made with the compounds prepared in examples 5-6
It is to be understood that the invention is not limited to the examples described above, but that modifications and variations may be effected thereto by those of ordinary skill in the art in light of the foregoing description, and that all such modifications and variations are intended to be within the scope of the invention as defined by the appended claims.
Claims (2)
1. A novel imidazole compound is characterized by having a structure shown as 001-017 as follows:
2. use of a compound according to claim 1 as a luminescent material in the preparation of an organic electroluminescent device.
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| CN109384726A (en) * | 2018-06-28 | 2019-02-26 | 吉林奥来德光电材料股份有限公司 | A kind of organic luminescent compounds and preparation method thereof and organic electroluminescence device |
| CN110854293B (en) * | 2018-12-10 | 2021-04-20 | 广州华睿光电材料有限公司 | Nitrogen heterocyclic compound, composition, high polymer and organic electroluminescent device |
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