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CN106892903B - Organic electroluminescent compound based on phenazine and carbazole and luminescent device thereof - Google Patents

Organic electroluminescent compound based on phenazine and carbazole and luminescent device thereof Download PDF

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CN106892903B
CN106892903B CN201710147312.9A CN201710147312A CN106892903B CN 106892903 B CN106892903 B CN 106892903B CN 201710147312 A CN201710147312 A CN 201710147312A CN 106892903 B CN106892903 B CN 106892903B
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organic electroluminescent
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CN106892903A (en
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黄锦海
苏建华
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Shanghai Hundred Biological Polytron Technologies Inc
Shanghai Taoe Chemical Technology Co Ltd
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Shanghai Hundred Biological Polytron Technologies Inc
Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The invention provides an organic electroluminescent compound based on phenazine and carbazole, which has good thermal stability, high luminous efficiency and high luminous purity, can be used for manufacturing an organic electroluminescent device, and is applied to the field of organic solar cells, organic thin film transistors or organic photoreceptors. The invention also provides an organic electroluminescent device which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of a light-emitting layer, a hole injection layer, a hole transport layer, an exciton blocking layer and an electron transport layer, and at least one of the organic layers comprises the compound shown in the structural formula I.

Description

Organic electroluminescent compound based on phenazine and carbazole and luminescent device thereof
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent compound based on phenazine and carbazole and an organic electroluminescent device thereof, belonging to the technical field of organic electroluminescent device display.
Background
Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic material between two metal electrodes by spin coating or vacuum evaporation, a classical three-layer organic electroluminescent device comprising a hole transport layer, a light emitting layer and an electron transport layer. Holes generated by the anode are combined with electrons generated by the cathode through the hole transport layer and the electron transport layer to form excitons in the light emitting layer, and then the excitons emit light. The organic electroluminescent device can be adjusted to emit various desired lights by changing the material of the light emitting layer as desired.
As a novel display technology, the organic electroluminescent device 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 invention at the end of the 20 th century and the 80 th era, organic electroluminescent devices have been used in industry, such as screens of cameras and mobile phones, but the current OLED devices have limited wider application due to low efficiency, short service life and other factors, especially large screen displays, and therefore, the efficiency of the devices needs to be improved. One of the important factors for the restriction is the performance of the organic electroluminescent material in the organic electroluminescent device. In addition, since the OLED device generates joule heat when operating under applied voltage, so that the organic material is easily crystallized, which affects the lifetime and efficiency of the device, it is also necessary to develop a stable and efficient organic electroluminescent material.
In the organic electroluminescent device, the introduction of the hole transport material and the injection material can effectively reduce the capability of positive charges transferred from the anode to the luminescent layer, and improve the efficiency and the thermal stability of the device. Conventional hole injection materials, such as copperphthalocyanines (cupc), are slow to degrade, consume high energy for fabrication, are not conducive to environmental protection, and absorb light, which affects device efficiency. The thermal stability of the original hole transport materials such as NPB is poor, and the service life of the device is also greatly influenced. Thus, development of highly efficient and stable organic electroluminescent materials is required.
Disclosure of Invention
The invention firstly provides an organic electroluminescent compound based on phenazine and carbazole, which is a compound with the following structural formula I:
Wherein n is selected from 1-5; a is selected from O, S, NR1、CR2R3，R1-R3Each independently selected from hydrogen, C1-C12 alkyl, C1-C8 alkoxy, C2-C8 substituted or unsubstituted alkenyl, C2-C8 substituted or unsubstituted alkynyl, and C6-C30 substituted or unsubstituted aryl.
Preferably, n is 1, 2 or 3.
R1Carbazolyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, (9, 9-dialkyl) fluorenyl, (9, 9-disubstituted or unsubstituted aryl) fluorenyl, 9-spirofluorenyl, triaryl (C6-C60) amine group, dibenzothienyl, dibenzofuranyl, preferably substituted with an alkyl group of C1-C12, substituted with an alkyl group of C1-C4, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, fluoranthenyl, (9, 9-disubstituted or unsubstituted); r2And R3Each independently is preferably selected from methyl, ethyl, propyl, butyl, isopropyl, isobutyl, isopentyl, hexyl, cyclohexyl, phenyl, biphenyl, tolyl.
Further preferably, the organic electroluminescent compounds according to the present invention are compounds of the following structural formulae 1 to 30:
The organic electroluminescent compound based on the phenazine and the carbazole can be applied to the fields of organic electroluminescent devices, organic solar cells, organic thin film transistors or organic photoreceptors.
The present invention also provides an organic electroluminescent device comprising an anode, a cathode and organic layers, the organic layers comprising at least one of a light-emitting layer, a hole injection layer, a hole transport layer, an exciton blocking layer, an electron transport layer, wherein at least one of the organic layers comprises a phenazine and carbazole based compound according to structural formula I:
Wherein n and A are as defined above.
Wherein the organic layer comprises a hole transport layer and a light emitting layer;
or the organic layer is a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer;
Or the organic layer is a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer and an electron injection layer;
Or the organic layer is a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and an exciton blocking layer;
Or the organic layer is a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer and an exciton blocking layer;
Or the organic layer is a hole transport layer, a light emitting layer, an electron injection layer and an exciton blocking layer.
Preferably, the layer in which the compound of formula I is located is a hole transport layer.
Preferably, the hole transport layer compound described by structural formula I is a compound of structural formula 1-30.
When the compound based on the phenazine and the carbazole as shown in the structural formula I is used for preparing a light-emitting device, the compound can be used alone or mixed with other compounds; the phenazine and carbazole based electroluminescent compounds of formula I may be used alone or in combination with two or more compounds of formula I.
In a further preferred mode, the organic electroluminescent device of the present invention comprises an anode, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein the hole transport layer contains at least one compound of formula I; further preferably, the hole transport layer contains at least one compound of formulae 1-30.
The total thickness of the organic layers of the organic electroluminescent device of the invention is 1 to 1000nm, preferably 50 to 500 nm.
When the compound with the structural formula I is used in the organic electroluminescent device, other materials can be matched and used, such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an exciton blocking layer and the like, so that blue light, green light, yellow light, red light or white light can be obtained.
The hole transport layer and the hole injection layer of the organic electroluminescent device have good hole transport performance of the required materials, and can effectively transport holes from the anode to the luminescent layer. In addition to the compounds described above with structural formula I, other small and high molecular organic compounds may be included, including but not limited to carbazoles, triarylamines, biphenyldiamines, fluorenes, phthalocyanines, hexacyano-hexaazatriphenylenes, 2,3,5, 6-tetrafluoro-7, 7',8,8' -tetracyanodimethyl-p-benzoquinone (F4-TCNQ), polyvinylcarbazole, polythiophene, polyethylene, or polyphenylsulfonic acid.
The light-emitting layer of the organic electroluminescent device has good light-emitting characteristics, and the range of visible light can be adjusted according to requirements. In addition to the compound of formula I of the present invention, the compound may also include, but is not limited to, naphthalene compounds, pyrene compounds, fluorene compounds, phenanthrene compounds, chrysene compounds, phenazine compounds, anthracene compounds, pentacene compounds, perylene compounds, diarylethene compounds, triphenylamine ethene compounds, amine compounds, carbazole compounds, benzimidazole compounds, furan compounds, organometallic fluorescent complexes, organometallic phosphorescent complexes (e.g., Ir, Pt, Os, Cu), polyvinylcarbazole, polyorganosiloxane compounds, polythiophene, and other organic polymer light emitting materials, which may be used alone or in combination of two or more.
The organic electron transport material of the organic electroluminescent device of the invention is required to have good electron transport performance, can effectively transport electrons from the cathode to the luminescent layer, and has high electron mobility. The following compounds may be selected, but are not limited thereto: oxazazole, thiazole compound, triazole compound, triazine compound, triazobenzene compound, quinoxaline compound, diazoanthracene compound, silicon-containing heterocyclic compound, quinoline compound, phenanthroline compound, and metal chelate (such as Alq)3) Fluorine-substituted benzene compounds and benzimidazole compounds.
The electron injection layer of the organic electroluminescent device of the present invention can effectively inject electrons from the cathode into the organic layer, and is mainly selected from compounds of alkali metals or alkali metals, or compounds of alkaline earth metals or alkali metal complexes, and the following compounds can be selected, but not limited thereto: alkali metals, alkaline earth metals, rare earth metals, oxides or halides of alkali metals, oxides or halides of alkaline earth metals, oxides or halides of rare earth metals, organic complexes of alkali metals or alkaline earth metals; lithium, lithium fluoride, lithium oxide, lithium nitride, 8-hydroxyquinoline lithium, cesium carbonate, 8-hydroxyquinoline cesium, calcium fluoride, calcium oxide, magnesium fluoride, magnesium carbonate, and magnesium oxide are preferable, and these compounds may be used alone or in a mixture, or may be used in combination with other organic electroluminescent materials.
Each of the organic layers in the organic electroluminescent device of the present invention can be prepared by a vacuum evaporation method, a molecular beam evaporation method, a dip coating method in a solvent, a spin coating method, a bar coating method, an inkjet printing method, or the like. For metal motors, evaporation or sputtering can be used for production.
Device experiments show that the compound based on phenazine and carbazole in the structural formula I has good thermal stability, high luminous efficiency, high luminous purity and low driving voltage. The organic electroluminescent device manufactured by the hole transport compound has the advantages of good electroluminescent efficiency, excellent color purity and long service life.
Drawings
FIG. 1 is a schematic structural diagram of an organic electroluminescent device according to the present invention;
Wherein 110 is a glass substrate, 120 is an anode, 130 is a hole transport layer, 140 is a light emitting layer, 150 is an electron transport layer, 160 is an electron injection layer, and 170 is a cathode.
Detailed Description
In order to describe the present invention in more detail, the following examples are given, but not limited thereto.
Example 1
Synthesis of Compound 1
Synthesis of intermediate 1-1
Adding N into the flasks respectively9,N10diphenylphenanthrene-9, 10-diamine (15g), p-bromoiodobenzene (11.77g), Cu (OTf)2(2.52g) and K2CO3(7.68g,55.6mol), trichlorobenzene (50g) was added, the mixture was heated to about 210 ℃ under mechanical stirring and refluxed overnight, after completion of the reaction, the heating was stopped, and the solvent was distilled off under reduced pressure. The column was used to give 4.02g of a pale yellow solid in 18.74% yield.
Synthesis of Compound 1
adding an intermediate 1-1(1g,2mmol), 7-dimethyl-5H-indeno [2,1-b ] carbazole (0.56g,2mmol), potassium carbonate (0.56g,4mmol), cuprous iodide (0.2g), phenanthroline (0.2g) and nitrobenzene (30mL) into a flask, heating and refluxing for 24 hours under the protection of nitrogen, cooling, adding dichloromethane, filtering, concentrating, and purifying a crude product by column chromatography to obtain 0.59g, wherein the yield is 42%.
example 2
Synthesis of Compound 6
Synthesis of intermediate 6-1
In a three-necked flask, 4-boronic acid-dibenzofuran (21g,0.1mol), o-bromonitrobenzene (20g,0.1mol), potassium carbonate (27.6g,0.2mol), palladium tetratriphenylphosphine (1g), tetrahydrofuran (300mL) and water (100mL) were added, heated under reflux for 12 hours under nitrogen protection, cooled, extracted with dichloromethane, dried, filtered, concentrated, stirred with methanol, filtered and dried to obtain 24g, yield 84%.
Synthesis of intermediate 6-2
Intermediate 6-1(10g,35mmol), o-dichlorobenzene (100mL), triethyl phosphite (50mL) were added to the flask, heated under reflux for 12 hours under nitrogen, cooled, and the solvent was removed under pressure, and the crude product was purified by column chromatography to give 6g, 67% yield.
Synthesis of Compound 6
the synthesis was the same as for compound 1, starting from intermediate 6-2 and intermediate 1-1, with a yield of 36%.
Example 3
Synthesis of Compound 17
Synthesis of intermediate 17-1
A reaction flask was charged with 7, 7-dimethyl-5H-indeno [2,1-b ] carbazole (10g,35.3mmol), p-bromoiodobenzene (12g,42mmol), potassium tert-butoxide (7.9g,70.6mmol), palladium acetate (0.3g,1.3mmol), tri-tert-butylphosphine tetrafluoroborate (0.8g,2.7mmol) and toluene (150mL), heated at reflux for 24 hours under nitrogen, cooled, toluene removed, dichloromethane added, washed with water, dried, and the crude product passed through the column to give 10g of product in 57% yield.
Synthesis of intermediate 17-2
Adding a compound 17-1(4.37g,10mmol), pinacol diborate (3.0g,12mmol), potassium acetate (3.0g), palladium dichlorotriphenylphosphine (50mg) and dioxane (60mL) into a single-neck flask, heating to 100 ℃ for reaction for 12h, passing through silica gel while hot, washing a filter cake with dichloromethane, evaporating the solvent by rotation, and purifying a crude product by column chromatography to obtain a product 2.8g with the yield of 60%.
synthesis of Compound 17
Intermediate 1-1(0.51g,1mmol), intermediate 17-2(0.48g,1mmol), tetrakistriphenylphosphine palladium (50mg), 2M aqueous potassium carbonate (10mL) and tetrahydrofuran (20mL) were charged in a flask, heated under reflux for 12 hours under nitrogen, cooled, extracted with dichloromethane, dried, concentrated, and the crude product was purified by column chromatography to give 0.43g of product in 54% yield.
Example 4
Synthesis of Compound 28
Synthesis of intermediate 28-1
The synthesis method is the same as that of the intermediate 17-1, and the raw materials are 11-phenyl-11, 12-indolino [2,3-a ] carbazole and p-bromoiodobenzene, and the yield is 45%.
Synthesis of intermediate 28-2
the synthesis method is the same as that of the intermediate 17-2, the raw material is the intermediate 1-1, and the yield is 63%.
Synthesis of Compound 28
The synthesis was the same as that of compound 17, starting from intermediate 28-1 and intermediate 28-2, in 54% yield.
Examples 5 to 8
Preparation of organic electroluminescent device
OLEDs were prepared using the compounds in the examples of the invention.
First, a transparent conductive ITO glass substrate 110 (with an anode 120 thereon) (south glass group ltd, china) is sequentially subjected to: deionized water, ethanol, acetone and deionized water, followed by oxygen plasma treatment for 30 seconds.
then, the present compound (table below) was evaporated to form a hole transport layer 130 having a thickness of 60 nm.
Then, a 30nm thick compound Alq was vapor-deposited on the hole transport layer3as the light emitting layer 140。
Then, Alq with a thickness of 20nm was deposited on the light-emitting layer by vapor deposition3As an electron transport layer 150. Finally, 1nm LiF is evaporated to form the electron injection layer 160 and 100nm Al is evaporated to form the device cathode 170.
The prepared devices were measured at maximum current efficiency using a Photo Research PR650 spectrometer as shown in the following table.
under the same conditions, the efficiency of the organic electroluminescent device prepared by using the organic electroluminescent compound of the present invention is higher than that of the comparative example. As described above, the compound of the present invention has high stability, and the organic electroluminescent device prepared by the present invention has low driving voltage, high efficiency and optical purity.
The structural formula in the device is as follows:
The foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.

Claims (7)

1. An organic electroluminescent compound based on phenazine and carbazole, characterized in that it is a compound of the following formulae 1, 6, 17, 28:
2. An organic electroluminescent device comprising an anode, a cathode and organic layers, the organic layers comprising at least one of a light-emitting layer, a hole injection layer, a hole transport layer, an exciton blocking layer, an electron transport layer, characterized in that at least one of the organic layers comprises the phenazine-and carbazole-based compound as claimed in claim 1.
3. The organic electroluminescent device according to claim 2, wherein the layer in which the phenazine-and carbazole-based compounds of structural formulae 1, 6, 17, and 18 are present is a hole transport layer.
4. The organic electroluminescent device as claimed in claim 2, wherein the phenazine and carbazole based compounds of structural formulae 1, 6, 17, 18 are used alone or in combination with other compounds.
5. The organic electroluminescent device according to claim 2, wherein the phenazine-and carbazole-based compounds of structural formulae 1, 6, 17, and 18 are used alone or in combination of two or more of the compounds of structural formulae 1, 6, 17, and 18.
6. The organic electroluminescent device according to claim 2, comprising an anode, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, characterized in that the hole transport layer contains at least one compound of the formulae 1, 6, 17, 18.
7. The organic electroluminescent device according to claim 2, comprising an anode, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, characterized in that the hole transport layer contains at least one compound of the formulae 1, 6, 17, 18.
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