CN111057014A - Organic electroluminescent compound, preparation method thereof and electroluminescent device - Google Patents

Organic electroluminescent compound, preparation method thereof and electroluminescent device Download PDF

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CN111057014A
CN111057014A CN201911379707.7A CN201911379707A CN111057014A CN 111057014 A CN111057014 A CN 111057014A CN 201911379707 A CN201911379707 A CN 201911379707A CN 111057014 A CN111057014 A CN 111057014A
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organic electroluminescent
organic
layer
electroluminescent compound
compound
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王辉
谢星冰
李贺
毕岩
杨冰
白金凤
马晓宇
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

The invention discloses an organic electroluminescent compound, which has a structural general formula shown as follows,

Description

Organic electroluminescent compound, preparation method thereof and electroluminescent device
Technical Field
The invention relates to the field of organic photoelectric materials, in particular to an organic electroluminescent compound, a preparation method thereof and an electroluminescent device.
Background
The organic electroluminescence technology is a latest generation display technology, and a light-emitting device prepared from an organic light-emitting material has the advantages of light weight, thinness, flexibility and the like in appearance, and particularly can be prepared into a flexible device which cannot be compared with other light-emitting materials. In the past decade, this technology has achieved some success on the way to commercialization, for example, organic electroluminescent diodes (OLEDs) have been applied to advanced displays for smart phones, televisions and digital cameras. Organic electroluminescent materials are the core and foundation of electroluminescent devices. The development of new materials is a source for promoting the continuous progress of the electroluminescent technology. The preparation of the original material and the optimization of the device are also the research hotspots of the organic electroluminescent industry at present.
OLED devices convert electrical energy into light by applying power to an organic light emitting material, and generally include an anode, a cathode, and an organic layer formed between the two electrodes. The organic layer further includes a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron blocking layer, a light emitting layer (containing a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like. Materials used in the organic layer may be further classified into a hole injection material, a hole transport material, a hole auxiliary material, a light emitting auxiliary material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport material, an electron injection material, and the like according to functions.
The light emitting layer material is required to have characteristics of high quantum efficiency, high mobility of electrons and holes, and uniformity and stability of the formed light emitting material layer. In recent years, development of a highly excellent light emitting material superior to conventional materials is urgently required. For this reason, there is a need for a material having high purity, good thermal stability, high electrochemical stability, and capable of improving the performance of the organic electroluminescent device, such as driving voltage, luminous efficiency, and lifetime characteristics.
Disclosure of Invention
In view of the above, the present invention provides an organic electroluminescent compound, a method for preparing the same, and an electroluminescent device. The quinoxaline derivative with the novel structure has the advantages that after the quinoxaline derivative is used for an organic electroluminescent device, the efficiency of the device is improved, and the service life is prolonged.
In order to achieve the purpose, the invention adopts the following technical scheme:
an organic electroluminescent compound, characterized by having a structural formula shown in chemical formula 1:
Figure BDA0002341941510000021
wherein:
r is substituted or unsubstituted C6-C18 aryl,
g is a substituted or unsubstituted heterocyclic group containing at least 1N from C16 to C40.
Preferably, the above aryl groups encompass monocyclic groups and polycyclic systems. Polycyclic rings can have two or more rings in which two carbons are common to two adjoining rings, where at least one of the rings is aromatic, e.g., the other rings can be cycloalkyl, cycloalkenyl, aryl, heteroaryl. The aryl is preferably aryl with 6-18 carbon atoms, and comprises benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene, fluorene and the like; in the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro ring structure. When the fluorenyl group is substituted, it may include a spirofluorenyl group, e.g.
Figure BDA0002341941510000022
And substituted fluorenyl radicals, e.g.
Figure BDA0002341941510000023
(9, 9-dimethylfluorenyl). However, the structure is not limited thereto. In addition, the aryl group may be optionally substituted, and preferably is one or more of hydrogen, deuterium, cyano, nitro, hydroxyl, mercapto and alkyl.
Preferably, the heterocyclic group includes monocyclic heterocyclic groups of one to three hetero atoms, such as pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine, pyrimidine and the like. Heterocyclyl also includes polycyclic ring systems having two or more rings in which two or four atoms (carbon or heteroatoms) are common to two or three adjoining rings, wherein at least one of the rings is heterocyclyl and the other rings can be cycloalkyl, cycloalkenyl, aryl, heterocycloalkyl, or heteroaryl. At least one heteroatom in the heterocyclic group is selected from the group consisting of N, O, S, P, B, Si, Se, Ge, but is not limited thereto, and is preferably N, O, S; the heterocyclic group may be optionally substituted.
Preferably, the heterocyclic group further includes substituted or unsubstituted C16-C40 spiroheterocyclic groups, and substituted or unsubstituted C16-C40 condensed heterocyclic groups.
Preferably, the heterocyclic group contains at least one N atom, and the N atom is bonded to the quinoxaline.
Preferably, the quinoxaline derivative represented by the above chemical formula 1 is selected from any one of the following structures:
Figure BDA0002341941510000031
Figure BDA0002341941510000041
Figure BDA0002341941510000051
Figure BDA0002341941510000061
the invention also provides a preparation method of the organic electroluminescent compound, which comprises the following steps:
chemical formula 1 synthetic route:
Figure BDA0002341941510000062
the specific synthesis steps of chemical formula 1 are as follows:
step 1: adding raw materials A (1-1.1 eq) and B (1eq) into a mixed solvent of THF and deionized water, adding alkali and a palladium catalyst under the protection of inert gas, and reacting at 90-100 ℃ for 19-21 h to obtain an intermediate C;
step 2: adding the intermediate C (1-1.3 eq) and the raw material D (1eq) into DMSO, adding alkali and a catalyst DMAP under the protection of inert gas, and reacting at 90-100 ℃ for 19-21 h to obtain an organic electroluminescent compound;
the number of the substituent groups and the number of the substituent groups in the above synthesis step are in accordance with the range defined in the organic electroluminescent compound.
The invention also provides an organic electroluminescent device containing the organic electroluminescent compound.
The organic electroluminescent device includes:
the organic electroluminescent device comprises a first electrode, a second electrode and one or more organic layers arranged between the two electrodes, wherein one or more layers of the organic layers contain the organic electroluminescent compound, and the organic electroluminescent compound can be in a single form or exist in the organic layers in a mixed manner with other substances.
Further, the organic layer at least comprises one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport technologies, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer having both electron transport and electron injection technologies.
Further, the organic electroluminescent device comprises at least one functional layer containing the organic electroluminescent compound.
Further, the organic electroluminescent device comprises a light-emitting layer, wherein the light-emitting layer contains the organic electroluminescent compound.
Further, the light-emitting layer of the organic electroluminescent device comprises a host material and a doping material, wherein the host material comprises a fluorescent host and a phosphorescent host, and the host material is the organic electroluminescent compound.
Further, the mixing ratio of the host material and the doping material of the light-emitting layer is 90:10 to 99.5:0.5, but not limited thereto.
Further, the organic material layer may have a multi-layered structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and the like, however, the structure is not limited thereto, and the organic material layer may have a single-layered structure.
Further, in manufacturing the organic electroluminescent device, the compound based on chemical formula 1 may be formed into an organic material layer by a solution coating method and a vacuum deposition method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, etc., but is not limited thereto.
Further, as the anode material, a material having a large work function is generally preferred so that holes are smoothly injected into the organic material layer. Specific examples of anode materials that can be used in the context of the present invention include: metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combinations of metals and oxides, such as ZnO: Al or SnO2: Sb; conductive polymers such as poly (3-methylthiophene), poly [3, 4- (ethylene-1, 2-dioxy) thiophene ] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
Further, as a cathode material, a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF/Al or LiO 2/Al; and the like, but are not limited thereto.
Further, the hole injecting material is a material that advantageously receives holes from the anode at low voltage, and the Highest Occupied Molecular Orbital (HOMO) of the hole injecting material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metalloporphyrin, oligothiophene, arylamine-based organic material, hexanenitrile-based hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and polyaniline-and polythiophene-based conductive polymer, and the like, but are not limited thereto, and may further include another compound capable of p-doping.
Further, the hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transporting the holes to the light emitting layer, and a material having high hole mobility is suitable. Specific examples thereof include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated portions and non-conjugated portions, and the like, but are not limited thereto.
Further, an electron blocking layer may be disposed between the hole transport layer and the light emitting layer. As the electron blocking layer, a material known in the art, for example, an arylamine-based organic material, may be used.
Further, the light emitting layer may emit red, green, or blue light, and may be formed of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in a visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include: 8-hydroxyquinoline aluminum complex (Alq 3); a carbazole-based compound; a di-polystyrene based compound; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole-based, benzothiazole-based, and benzimidazole-based compounds; polymers based on poly (p-phenylene vinylene) (PPV); a spiro compound; a polyfluorene; rubrene, and the like, but is not limited thereto.
Further, the host material of the light-emitting layer includes a condensed aromatic ring derivative, a heterocyclic ring-containing compound, and the like. Which includes the above organic electroluminescent compounds.
The doping material used as the light-emitting layer is an iridium-based complex.
Further, a hole blocking layer may be disposed between the electron transport layer and the light emitting layer, and a material known in the art, for example, a triazine-based compound may be used.
Further, the electron transport layer may function to facilitate electron transport. The electron transport material is a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer, and a material having high electron mobility is suitable. Specific examples thereof include: al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; a hydroxyflavone-metal complex; and the like, but are not limited thereto.
Further, the thickness of the electron transport layer may be 1nm to 50 nm.
The electron transport layer having a thickness of 1nm or more has an advantage of preventing the electron transport property from being degraded, and the electron transport layer having a thickness of 50nm or less has an advantage of preventing the driving voltage for enhancing electron transfer from being increased due to the electron transport layer being too thick.
Further, the electron injection layer may function to promote electron injection. The electron injecting material is preferably a compound having the following functions: it has an ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from migrating to a hole injection layer, and, in addition, has an excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and the like and derivatives thereof, metal complexes, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
The organic light emitting device may be a top emission type, a bottom emission type, or a double-side emission type depending on the material used.
The organic electroluminescent device can be used for organic luminescent devices, organic solar cells, electronic paper, organic photoreceptors or organic thin film transistors.
According to the technical scheme, compared with the prior art, the organic electroluminescent compound has the characteristics of high purity, high thermal stability and high electrochemical stability, and the efficiency and the service life of the device can be improved after the organic electroluminescent compound is used for an organic electroluminescent device.
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
Preparation of Compound F003
Figure BDA0002341941510000111
Step 1, weighing A003(110.53mmol,24.54g) and B003(100.49mmol,20g) into a reaction system under the protection of nitrogen, adding a mixed solution of 490mL of tetrahydrofuran and 490mL of purified water, adding potassium carbonate (301.46mmol,41.66g) and tetrakis (triphenylphosphine) palladium (2.01mmol,2.32g) under the protection of nitrogen, refluxing at 90-100 ℃ for 19h under the protection of nitrogen, cooling to room temperature, separating liquid, drying an organic phase, filtering, performing column chromatography purification, and performing spin-drying to obtain an intermediate C003(18.4g, the yield is 53.73%).
Step 2, weighing the intermediates C003(52.82mmol,18g) and D003(40.63mmol,10.45g) under a nitrogen protection system, adding 100mL of dimethyl sulfoxide, adding cesium carbonate (121.88mmol,39.71g) and DMAP (2.03mmol,248.17mg) under nitrogen protection, refluxing for 19h at 90-100 ℃ under nitrogen protection, cooling to room temperature to precipitate a solid, performing suction filtration, dissolving the solid with toluene, filtering with a silica gel funnel, and spin-drying the filtrate to obtain a solid, and recrystallizing the solid with ethyl acetate to obtain the final compound F003(14.6g, 63.98% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 561.64; the test value was 561.18.
Example 2
Preparation of Compound F008
Figure BDA0002341941510000121
Step 1, weighing A008(110.53mmol,16.24g) and B008(100.49mmol,20g) in a nitrogen protection system, adding a mixed solution of 490mL tetrahydrofuran and 490mL purified water, adding potassium carbonate (301.46mmol,41.66g) and tetrakis (triphenylphosphine) palladium (2.01mmol,2.32g) in the nitrogen protection system, refluxing at 90-100 ℃ for 20h in the nitrogen protection system, cooling to room temperature, separating liquid, drying an organic phase, filtering, performing column chromatography purification, and performing spin drying to obtain an intermediate C008(15.3g, and the yield is 57.3%).
Step 2, weighing the intermediates C008(56.45mmol,15g) and D008(43.43mmol,12.26g) under a nitrogen protection system, adding 100mL of dimethyl sulfoxide, adding cesium carbonate (130.28mmol,42.45g), DMAP (2.17mmol,265.27mg) under nitrogen protection, refluxing for 20h at 90-100 ℃ under nitrogen protection, cooling to room temperature, separating out a solid, performing suction filtration, dissolving the solid with toluene, filtering with a silica gel funnel, and spin-drying the filtrate to obtain a solid, and recrystallizing the solid with ethyl acetate to obtain the final compound F008(15.2g, yield 68.42%).
HPLC purity is more than 99%.
Mass spectrum calculated 511.18; the test value was 511.59.
Example 3
Preparation of Compound F011
Figure BDA0002341941510000131
Step 1, weighing A011(110.53mmol,13.48g) and B011(100.49mmol,20g) into a reaction system under the protection of nitrogen, adding a mixed solution of 490mL tetrahydrofuran and 490mL purified water, adding potassium carbonate (301.46mmol,41.66g) and tetrakis (triphenylphosphine) palladium (2.01mmol,2.32g) under the protection of nitrogen, refluxing at 90-100 ℃ for 21h under the protection of nitrogen, cooling to room temperature, separating liquid, drying an organic phase, filtering, performing column chromatography purification, and performing spin drying to obtain an intermediate C011(13.4g, the yield is 55.4%).
Step 2, weighing intermediate C011(54.01mmol,13g) and D011(41.55mmol,13.77g) under a nitrogen protection system, adding 100mL dimethyl sulfoxide, adding cesium carbonate (124.64mmol,40.61g) and DMAP (2.08mmol,253.79mg) under nitrogen protection, refluxing for 21h at 90-100 ℃ under nitrogen protection, cooling to room temperature to separate out a solid, performing suction filtration, dissolving the solid with toluene, filtering with a silica gel funnel, and spin-drying the filtrate to obtain a solid, and recrystallizing the solid with ethyl acetate to obtain the final compound F011(14.2g, 63.81% of yield).
HPLC purity is more than 99%.
Mass spectrum calculated 535.65; the test value was 535.20.
Example 4
Preparation of Compound F014
Figure BDA0002341941510000141
Step 1, weighing A014(110.53mmol,14.03g) and B014(100.49mmol,20g) into a reaction system under the protection of nitrogen, adding a mixed solution of 490mL tetrahydrofuran and 490mL purified water, adding potassium carbonate (301.46mmol,41.66g) and tetrakis (triphenylphosphine) palladium (2.01mmol,2.32g) under the protection of nitrogen, refluxing at 90-100 ℃ for 20h, cooling to room temperature, separating the liquid, drying the organic phase, filtering, spin-drying, purifying by column chromatography, and spin-drying to obtain an intermediate C014(14.2g, yield 57.5%).
Step 2, weighing intermediates C014(56.98mmol,14g) and D014(43.83mmol,12.77g) under a nitrogen protection system, adding 100mL of dimethyl sulfoxide, adding cesium carbonate (131.48mmol,42.84g), DMAP (2.19mmol,267.72mg) under a nitrogen protection system, refluxing at 90 ℃ to 100 ℃ for 20h, cooling to room temperature to precipitate a solid, performing suction filtration, dissolving the solid with toluene, filtering with a silica gel funnel, and spin-drying the filtrate to obtain a solid, which is recrystallized with ethyl acetate to obtain final compound F014(12.8g, 58.34% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 500.62; the test value was 500.20.
Example 5
Preparation of Compound F019
Figure BDA0002341941510000151
Step 1, weighing A019(110.53mmol,27.2g) and B019(100.49mmol,20g) in a nitrogen protection system, adding a mixed solution of 490mL tetrahydrofuran and 490mL purified water, adding potassium carbonate (301.46mmol,41.66g) and tetrakis (triphenylphosphine) palladium (2.01mmol,2.32g) in a nitrogen protection system, refluxing at 90-100 ℃ for 20h, cooling to room temperature, separating liquid, drying an organic phase, filtering, spin-drying, purifying by column chromatography, and spin-drying to obtain intermediate C019(20.7g, yield 56.46%).
Step 2, weighing intermediate C019(54.82mmol,20g) and D019(42.17mmol,13.98g) under a nitrogen protection system, adding 100mL of dimethyl sulfoxide, adding cesium carbonate (126.51mmol,41.22g), DMAP (2.11mmol,257.59mg) under nitrogen protection, refluxing for 20h at 90-100 ℃ under nitrogen protection, cooling to room temperature, separating out a solid, performing suction filtration, dissolving the solid with toluene, filtering with a silica gel funnel, and spin-drying the filtrate to obtain a solid, and recrystallizing the solid with ethyl acetate to obtain final compound F019(15.4g, 55.35% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 659.79; the test value was 659.24.
The synthesis methods of other compounds are the same as the above examples, which are not repeated herein, and the mass spectra and molecular formulas of other synthesis examples are shown in table 1:
TABLE 1
Figure BDA0002341941510000161
Example 6
An organic electroluminescent device was prepared using the compound F003 prepared in example 1, specifically:
coating with a thickness of
Figure BDA0002341941510000162
The ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. Firstly, evaporating 4,4', 4' -tri (N-3-methylphenyl-N-phenylamino) triphenylamine (m-MTDATA) on an ITO (anode)
Figure BDA0002341941510000163
As the hole injection layer, N-bis (1-naphthyl) -N, N ' -diphenyl- (1,1' -biphenyl) -4,4' -diamine (NPB) was vacuum-evaporated immediately above the formed hole injection layer
Figure BDA0002341941510000164
As a hole transport layer. Evaporating the main body material F003 and the doping material Ir (bty)2acac on the hole transport layer in a weight ratio of 95:5
Figure BDA0002341941510000165
Then, an electron transport layer "Alq3" was vacuum-deposited on the light-emitting layer in this order "
Figure BDA0002341941510000166
Vapor deposition of electron injection layer
Figure BDA0002341941510000171
Evaporation cathode
Figure BDA0002341941510000172
And preparing the organic electroluminescent device. The performance luminescence characteristics of the obtained device are tested by adopting a KEITHLEY2400 type source measuring unit and a CS-2000 spectral radiance luminance meter to evaluate the driving voltage and the luminescence efficiency.
Figure BDA0002341941510000173
Example 7
By referring to the above method, the organic electroluminescent devices of the corresponding compounds were prepared by replacing the compound F003 with F008, F011, F014, F019, F022, F024, F026, F030, F033, F035, F038, F040, F042, respectively.
Comparative example 1
An organic electroluminescent device was prepared in the same manner as in example 6, and the structure of the host material compound of the light-emitting layer was as follows:
Figure BDA0002341941510000174
Figure BDA0002341941510000181
the same examination as in example 6 was performed on the prepared organic electroluminescent device, and the results are shown in table 2.
TABLE 2
Detection result of organic electroluminescent device
Figure BDA0002341941510000182
As can be seen from table 1, the organic electroluminescent device prepared using the compound provided by the present invention as the host material of the light-emitting layer has a significantly reduced driving voltage, and significantly improved luminous efficiency and lifetime, as compared to the organic electroluminescent device prepared using the comparative compound CBP as the host material of the light-emitting layer.
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 by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
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 electroluminescent compound, wherein the structural general formula of the organic electroluminescent compound is shown in chemical formula 1:
Figure FDA0002341941500000011
wherein:
r is C6-C18 aryl;
g is a heterocyclic group of C16-C40.
2. The organic electroluminescent compound of claim 1, wherein the C6-C18 aryl group is benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, pyrene, or fluorene.
3. An organic electroluminescent compound according to claim 2, wherein the C6-C18 aryl group may be optionally substituted.
4. The organic electroluminescent compound as claimed in claim 1, wherein the C16-C40 heterocyclic group includes C16-C40 spiro heterocyclic group and C16-C40 fused heterocyclic group.
5. The organic electroluminescent compound as claimed in claim 4, wherein the C16-C40 heterocyclic group has at least one N atom, and the N atom is bonded to quinoxaline.
6. A method for producing an organic electroluminescent compound as claimed in any one of claims 1 to 5, comprising the steps of:
step 1: adding the raw materials A and B into a mixed solvent of THF and deionized water, adding alkali and a palladium catalyst under the protection of inert gas, and reacting at 90-100 ℃ for 19-21 h to obtain an intermediate C;
step 2: adding the intermediate C and the raw material D into DMSO, adding alkali and a catalyst DMAP under the protection of inert gas, and reacting at 90-100 ℃ for 19-21 h to obtain an organic electroluminescent compound;
Figure FDA0002341941500000021
r, G in the above formula is represented by the same moiety as in the chemical formula 1 according to any one of claims 1 to 5.
7. The method according to claim 6, wherein the amount of the raw material A is 1 to 1.1eq, the amount of the raw material B is 1eq, the amount of the intermediate C is 1 to 1.3eq, and the amount of the raw material D is 1 eq.
8. An organic electroluminescent device comprising an organic electroluminescent compound, comprising: a first electrode, a second electrode, one or more organic layers disposed between the first electrode and the second electrode;
the organic layer contains the organic electroluminescent compound according to claim 1.
9. The organic electroluminescent device according to claim 8, wherein the organic layer comprises at least one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport techniques, 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 techniques;
the light-emitting layer comprises a main material and a doping material, the main material is the organic electroluminescent compound disclosed by any one of claims 1-5, and the mixing ratio of the main material to the doping material is 90: 10-99.5: 0.5.
10. Use of the organic electroluminescent device comprising the organic electroluminescent compound according to claim 9 for the production of an organic electroluminescent device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
CN201911379707.7A 2019-12-27 2019-12-27 Organic electroluminescent compound, preparation method thereof and electroluminescent device Pending CN111057014A (en)

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