CN114262328A - Organic electroluminescent compound, preparation method thereof and organic electroluminescent device - Google Patents
Organic electroluminescent compound, preparation method thereof and organic electroluminescent device Download PDFInfo
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Abstract
The invention relates to an organic electroluminescent compound, a preparation method thereof and an organic electroluminescent device, belonging to the technical field of organic photoelectric luminescent materials, wherein the pi conjugated effect in the organic electroluminescent compound enables the organic electroluminescent compound to have strong hole transmission capability; when the organic electroluminescent compound is used as a hole transport material or other organic compound layers of an OLED (organic light emitting diode) luminescent device, the high hole transport rate can reduce the initial voltage of the device, improve the efficiency of the organic electroluminescent device and prolong the service life well.
Description
Technical Field
The invention relates to the technical field of organic photoelectric luminescent materials, in particular to an organic electroluminescent compound, a preparation method thereof and an organic electroluminescent device.
Background
The organic electroluminescent material is a high molecular or small molecular organic material capable of emitting light under the action of an electric field. Organic electroluminescent devices (OLEDs) have high brightness, high resolution, wide viewing angles, and low power consumption, and have become a research hotspot. The novel flat panel display device can meet the requirements of people, has the advantages of wide working temperature, capability of realizing flexible display and the like, and becomes a new pet for the new generation of flat panel display.
Organic light emitting diodes generally have the following structure: an anode, a cathode, and an organic material layer therebetween. In order to improve efficiency and stability of the organic EL element, the organic material layer includes a plurality of layers having different materials, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), a light emission auxiliary layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an Electron Transport Layer (ETL), and an Electron Injection Layer (EIL). Among them, a layer having a function of transporting holes, such as a hole injection layer, a hole transport layer, an electron blocking layer, and the like, can change hole transport efficiency from holes to a light emitting layer, light emitting efficiency, lifetime, and the like, and has a great influence on performance data of an electronic device.
The light-emitting auxiliary layer can play a role in reducing potential barrier between the hole transport layer and the light-emitting layer, reducing the driving voltage of the organic electroluminescent device and further increasing the utilization rate of holes, thereby improving the luminous efficiency and the service life of the device and reducing the driving voltage. However, the existing functional materials capable of forming the light-emitting auxiliary layer are few, and particularly, the service life and the light-emitting efficiency of the OLED are not obviously improved, the glass transition temperature is low, and the like.
Disclosure of Invention
The present invention is directed to an organic electroluminescent compound, a method for preparing the same, and an organic electroluminescent device, which solve the problems set forth in the background art.
In order to achieve the purpose, the invention provides the following technical scheme:
the organic electroluminescent compound has the following structural general formula:
in the formula:
R1、R2、R5the substitution position is a benzene ringThe number of the substituted optional positions is an integer of 0 to 4;
R3、R4the substituted position is any substituted position on the benzene ring, and the number of the substituted positions is an integer of 0-3;
R1-R5each independently is one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monocyclic or polycyclic C3-C30 aliphatic ring or aromatic ring connected to an adjacent substituent;
Ar1、Ar2each independently is one of a substituted or unsubstituted C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy, a C3-C30 aliphatic ring or a 3-to 30-membered aromatic ring connected to adjacent substituents to form a mono-or polycyclic ring;
l is a bond, substituted or unsubstituted C6-C30 aryl.
As a further aspect of the present invention, said Ar is1、Ar2Each independently is a substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 3-to 26-membered heteroaryl; at least one carbon atom in the monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 30-membered aromatic ring that is linked to an adjacent substituent is replaced or not replaced with a heteroatom.
As a further aspect of the present invention, Ar is1、Ar2Each independently is substituted or unsubstituted C10-C14 aryl, substituted or unsubstituted 18-to 22-membered heteroaryl; the heteroatom is one of nitrogen, oxygen or sulfur.
As a further technical solution of the present invention, L is benzene or deuterated benzene.
As still further technical solution of the present invention, the organic electroluminescent compound is one of formula 1 to formula 107:
a preparation method of an organic electroluminescent compound comprises the following steps:
dissolving the raw material 2 in THF, ventilating for three times, cooling to-70 to-80 deg.C, slowly adding N-BuLi, reacting for 1-3h, and reacting2Adding the raw material 1 under protection, slowly heating to 20-30 ℃, and stirring for 8-10h to prepare an intermediate 1;
adding the intermediate 1 into a reaction bottle, adding glacial acetic acid, heating to 60-80 ℃, and dropwise adding concentrated sulfuric acid to prepare an intermediate 2;
preparation of chemical formula 1
Adding the intermediate 2 and the raw material 3 into a mixed solution of toluene, ethanol and water, then ventilating for three times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, uniformly stirring, heating to 90-100 ℃, and reacting for 8-10 hours to prepare a chemical formula 1;
② preparation of chemical formula 2
Adding the intermediate 2 and the raw material 4 into a toluene solution, then ventilating for three times, adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under the protection of nitrogen, uniformly stirring, heating to 110 ℃, and reacting for 7-10h to obtain a chemical formula 2;
the synthetic route is as follows:
wherein R is1-R5、Ar1、Ar2And L is as defined above for formula 1.
In the above technical solution, the step 1 specifically includes the following steps: dissolving the raw material 2 in THF, ventilating for 3 times, cooling to-70 to-80 deg.C, slowly adding N-BuLi, reacting for 1-3h, and reacting2Adding the raw material 1 under protection, slowly heating to 20-30 ℃, stirring for 8-10h, then slowly adding distilled water into the reaction solution to quench the reaction, and extracting the reaction solution with DCM; the extracted organic layer was then dried with magnesium sulfate and the solvent was removed using a rotary evaporator; the solid was precipitated with DCM and PE (1: 6 by volume) to give intermediate 1.
In the above technical solution, the step 2 specifically includes the following steps:
adding the intermediate 1 into a reaction bottle, adding glacial acetic acid with the volume of 10 times, heating to 60-80 ℃, slowly dropwise adding concentrated sulfuric acid (with the volume of 1 time), finishing the reaction after dropwise adding, then adding distilled water with the volume of 20 times of concentrated sulfuric acid, and completely precipitating solids, filtering and drying to obtain an intermediate 2.
In the above technical solution, the step 3 specifically includes the following steps:
preparation of chemical formula 1
Adding the intermediate 2 and the raw material 3 into a mixed solution of toluene ethanol and water, then ventilating for 3 times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, stirring uniformly, heating to 90-100 ℃, reacting for 8-10h, and then extracting the mixture by using dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; purifying the remaining material by column chromatography to obtain the compound represented by chemical formula 1.
② preparation of chemical formula 2
Adding the intermediate 3 and the raw material 4 into a toluene solution, then ventilating for 3 times, adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under the protection of nitrogen, stirring uniformly, heating to 110 ℃, reacting for 7-10h, and then extracting the mixture by using dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography to obtain the compound represented by chemical formula 2.
An organic electroluminescent device comprising a first electrode, a second electrode and an organic compound layer interposed between the two electrodes, characterized in that the organic compound layer comprises a hole transport layer comprising any of the organic electroluminescent compounds described in the present invention.
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 has high hole mobility.
Preferably, one or more layers selected from a hole injection layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer are further included.
Preferably, the first electrode acts as an anode, the anode preferably comprising a material having a high work function. Such as Indium Tin Oxide (ITO) or Indium Zinc Oxide (IZO). Since the lifetime of the device of the invention is shortened in the presence of water and/or air, the device is suitably (depending on the application) structured, provided with contacts and finally sealed.
The 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, can be used.
The material of the light emitting layer is a material capable of emitting visible light by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the received holes and electrons.
The light-emitting layer comprises a host material and a doping material;
the mass ratio of the main material to the doping material is 90-99.5: 0.5-10;
the host material comprises a fluorescent host and a phosphorescent host;
the doping material comprises fluorescent doping and phosphorescent doping;
as the hole-blocking layer material, a compound having a hole-blocking effect known in the art, for example, a phenanthroline derivative such as Bathocuproine (BCP), an oxazole derivative, a triazole derivative, a triazine derivative, or the like can be used, but the invention is not limited thereto.
The electron transport layer may function to facilitate electron transport. Compounds having an electron transporting action well known in the art, for example, Al complexes of 8-hydroxyquinoline; a complex comprising Alq 3; an organic radical compound; hydroxyflavone-metal complexes, and the like.
The electron injection layer may function to promote electron injection. Has the ability of transporting electrons and prevents excitons generated in the light emitting layer from migrating to the hole injection layer. The electron injecting material used in the present invention includes 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 five-membered ring derivatives, and the like, but is not limited thereto.
The second electrode serves as a cathode, and a material having a small work function is generally preferred so that electrons are smoothly injected into the organic material layer. Such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof.
Compared with the prior art, the invention has the beneficial effects that: the pi conjugated effect in the organic electroluminescent compound enables the organic electroluminescent compound to have strong hole transmission capability; when the organic electroluminescent compound is used as a hole transport material of an OLED (organic light emitting diode) luminescent device or other organic compound layers, the high hole transport rate can reduce the initial voltage of the device, improve the efficiency of the organic electroluminescent device and prolong the service life well.
Detailed Description
An organic electroluminescent compound, which has a structural general formula as follows:
the reaction route of the preparation method of the organic electroluminescent compound is as follows:
example 1
The preparation method of the organic electroluminescent compound adopts the synthesis route and comprises the following steps:
adding raw material 2(44.6mmol) and 100ml THF into a reaction vessel, ventilating for 3 times, cooling to-78 deg.C, adding 2.5mol/L n-BuLi (17.8ml, 44.6mmol) under nitrogen atmosphere, stirring for 2h, adding raw material 1(37mmol), heating to 25 deg.C, stirring for 10h, and finishing the reaction. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator and a solid was precipitated with DCM and PE (volume ratio 1: 6) to yield intermediate 1(14.0g, 74.5% yield, MW: 508.11).
Adding the intermediate 1(26.2mmol) into a reaction bottle, adding 240ml of glacial acetic acid, heating to 80 ℃, dropwise adding 12ml of concentrated sulfuric acid, finishing the reaction after the dropwise adding is finished, then adding 240ml of distilled water, separating out a solid, and drying to obtain an intermediate 2 (9.8g, the yield is 76.3%, and the MW: 490.08).
Adding the intermediate 2(18.1mmol) and the raw material 3(21.8mmol) into 300ml of toluene solution, then ventilating for 3 times, adding a palladium catalyst (0.181mmol), tri-tert-butylphosphine (0.905mmol) and sodium tert-butoxide (36.2mmol) under the protection of nitrogen, stirring uniformly, heating to 110 ℃, reacting for 10h, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1: 11) to obtain the organic electroluminescent compound, see formula 8(10.8g, 73.2% yield, MW:815.09), scheme as follows:
example 2
The preparation method of the organic electroluminescent compound adopts the synthesis route and comprises the following steps:
adding raw material 2(44.6mmol) and 100ml THF into a reaction vessel, ventilating for 3 times, cooling to-78 deg.C, adding 2.5mol/L n-BuLi (17.8ml, 44.6mmol) under nitrogen atmosphere, stirring for 2h, adding raw material 1(37mmol), heating to 25 deg.C, stirring for 10h, and finishing the reaction. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator and the solid precipitated with DCM and PE (1: 6) to give intermediate 1(12.6g, 74.4% yield, MW: 457.90).
Adding the intermediate 1(26.2mmol) into a reaction bottle, adding 240ml of glacial acetic acid, heating to 80 ℃, dropwise adding 12ml of concentrated sulfuric acid, finishing the reaction after the dropwise adding is finished, then adding 240ml of distilled water, separating out a solid, and drying to obtain an intermediate 2 (9.6g, the yield is 74.2%, and the MW: 439.91).
Adding the intermediate 2(18.1mmol) and the raw material 3(21.8mmol) into a mixed solution of toluene (180ml), ethanol (60ml) and water (60ml), then ventilating for 3 times, adding a palladium catalyst (0.181mmol) and potassium carbonate (54.3mmol), stirring uniformly, heating to 100 ℃, reacting for 10h, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried using sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1: 11) to obtain the organic electroluminescent compound, see formula 21(8.3g, 70.7% yield, MW:648.90), scheme as follows:
example 3
The preparation method of the organic electroluminescent compound adopts the synthesis route and comprises the following steps:
adding raw material 2(44.6mmol) and 100ml THF into a reaction vessel, ventilating for 3 times, cooling to-78 deg.C, adding 2.5mol/L n-BuLi (17.8ml, 44.6mmol) under nitrogen atmosphere, stirring for 2h, adding raw material 1(37mmol), heating to 25 deg.C, stirring for 10h, and finishing the reaction. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator and a solid was precipitated with DCM and PE (volume ratio 1: 6) to yield intermediate 1(14.1g, 74.1% yield, MW: 514.10).
Adding the intermediate 1(26.2mmol) into a reaction bottle, adding 240ml of glacial acetic acid, heating to 80 ℃, dropwise adding 12ml of concentrated sulfuric acid, finishing the reaction after the dropwise adding is finished, then adding 240ml of distilled water, separating out a solid, and drying to obtain an intermediate 2 (9.5g, the yield is 73.1%, and the MW: 496.08).
Adding the intermediate 2(18.1mmol) and the raw material 3(21.8mmol) into a mixed solution of toluene (180ml), ethanol (60ml) and water (60ml), then ventilating for 3 times, adding a palladium catalyst (0.181mmol) and potassium carbonate (54.3mmol), stirring uniformly, heating to 100 ℃, reacting for 10h, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried using sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1: 11) to obtain the organic electroluminescent compound, see formula 30(10.3g, 69.3% yield, MW:821.13), scheme as follows:
example 4
The preparation method of the organic electroluminescent compound adopts the synthesis route and comprises the following steps:
adding raw material 2(44.6mmol) and 100ml THF into a reaction vessel, ventilating for 3 times, cooling to-78 deg.C, adding 2.5mol/L n-BuLi (17.8ml, 44.6mmol) under nitrogen atmosphere, stirring for 2h, adding raw material 1(37mmol), heating to 25 deg.C, stirring for 10h, and finishing the reaction. Distilled water was then added to the reaction solution to quench the reaction, and the reaction solution was extracted with DCM. The extracted organic layer was then dried over magnesium sulfate and the solvent was removed using a rotary evaporator and a solid was precipitated with DCM and PE (volume ratio 1: 6) to yield intermediate 1(12.5g, 73.4% yield, MW: 457.89).
Adding the intermediate 1(26.2mmol) into a reaction bottle, adding 240ml of glacial acetic acid, heating to 80 ℃, dropwise adding 12ml of concentrated sulfuric acid, finishing the reaction after the dropwise adding is finished, then adding 240ml of distilled water, separating out a solid, and drying to obtain an intermediate 2 (8.5g, the yield is 73.7%, and the MW: 439.97).
Adding the intermediate 2(18.1mmol) and the raw material 3(21.8mmol) into 300ml of toluene solution, then ventilating for 3 times, adding a palladium catalyst (0.181mmol), tri-tert-butylphosphine (0.905mmol) and sodium tert-butoxide (36.2mmol) under the protection of nitrogen, stirring uniformly, heating to 110 ℃, reacting for 10h, and then extracting the mixture with dichloromethane and water; the extracted organic layer was then dried with sodium sulfate and the solvent was removed using a rotary evaporator; the remaining material was purified by column chromatography (volume ratio of DCM to PE 1: 11) to obtain the organic electroluminescent compound, see formula 72(9.9g, 70.0% yield, MW:780.93), scheme below:
examples 5 to 24
The synthesis of compounds 1, 6, 11, 16, 19, 23, 34,36,46, 48, 52, 55, 60, 62,66, 74, 79, 91, 101, 105 was completed according to the synthesis method of example 1, and the mass spectra and molecular formulae and yields of examples 5-24 are shown in table 1 below. In addition, other compounds of the present application can be obtained by the synthetic methods described in the above-mentioned examples.
TABLE 1
Application example 1
An organic electroluminescent device is prepared by the following method:
a. an ITO anode: cleaning an ITO (indium tin oxide) -Ag-ITO (indium tin oxide) glass substrate with the coating thickness of 150nm in distilled water for 2 times, ultrasonically cleaning for 30min, repeatedly cleaning for 2 times by using distilled water, ultrasonically cleaning for 10min, after cleaning, ultrasonically cleaning with methanol, acetone and isopropanol in sequence (cleaning for 5min each time), drying, then transferring to a plasma cleaning machine for cleaning for 5min, then transferring to an evaporation plating machine, taking the substrate as an anode, and sequentially evaporating other functional layers on the substrate;
b. HIL (hole injection layer): the hole transport layer material HT and the P-dopant used by the device are formed by evaporation together, and the chemical formula of the P-dopant is shown as follows; the evaporation rate is
The evaporation rate ratio of HT to P-dopant is 97: 3, the thickness is 10 nm;
c. HTL (hole transport layer): to be provided with
Vacuum deposition of 120nm of the compound 8 provided in the above example as a hole transport layer on top of the hole injection layer;
d. EML (light-emitting layer): then on the above-mentioned hole transport layer to
The Host material (Host) and the Dopant material (Dopant) are vacuum-deposited to a thickness of 25nm as the light-emitting layer, wherein Host and Dopa are usednt has the following chemical formula; wherein the evaporation rate ratio of Host to Dopantt is 98: 2;
e. HB (hole blocking layer): to be provided with
The evaporation rate of (2) and vacuum evaporation of a hole blocking layer with the thickness of 5.0 nm;
f. ETL (electron transport layer): to be provided with
The evaporation rate of (3), ET and Liq with the thickness of 30nm are evaporated in vacuum to be used as electron transmission layers, and the chemical formula of the ET is shown as follows; wherein the evaporation rate ratio of ET to Liq is 50: 50;
g. EIL (electron injection layer): to be provided with
The evaporation rate of (1.0 nm) of the Yb film layer is evaporated to form an electron injection layer;
h. cathode: to be provided with
The evaporation rate ratio of the (1) to the (9) is 18nm, and the evaporation rate ratio of magnesium to silver is 1:9, so that an OLED device is obtained;
i. light extraction layer: to be provided with
The evaporation rate of (3), CPL with a thickness of 70nm was vacuum evaporated on the cathode as a light extraction layer;
j. and packaging the evaporated substrate. Firstly, coating the cleaned back cover plate by using UV glue through gluing equipment, then moving the coated cover plate to a pressing working section, placing the evaporated substrate on the upper end of the cover plate, finally, attaching the substrate and the cover plate under the action of attaching equipment, and simultaneously, finishing the illumination and solidification of the UV glue.
Comparative example 1
According to the method of application example 1, the material of the hole transport layer is replaced by chemical A from the compound in application example 1, and the material of the hole injection layer is adaptively adjusted; the structural formula of compound a is as follows:
comparative example 2
According to the method of application example 1, the material of the hole transport layer is replaced by the chemical compound B in application example 1, and the material of the hole injection layer is adaptively adjusted; the structural formula of compound B is as follows:
the organic electroluminescent devices obtained in the comparative examples of the devices according to the above-mentioned device examples were characterized at a luminance of 1000(nits) for driving voltage, luminous efficiency, BI value and lifetime, and the test results are shown in the following table 2:
TABLE 2
As can be seen from Table 2, the pi-conjugation effect in the organic electroluminescent compounds proposed by the present invention makes them have a strong hole transport ability. When the organic electroluminescent compound is used as a hole transport material or other organic compound layers of an OLED (organic light emitting diode) luminescent device, the driving voltage of the device can be reduced, the efficiency of the organic electroluminescent device is improved, and meanwhile, the rigid nut core structure of the organic electroluminescent compound enables the corresponding compound to have good structural stability and the service life of the device is well prolonged.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein.
Furthermore, it should be understood that although the present description refers to embodiments, not every embodiment may contain only a single embodiment, and such description is for clarity only, and those skilled in the art should integrate the description, and the embodiments may be combined as appropriate to form other embodiments understood by those skilled in the art.
Claims (8)
1. An organic electroluminescent compound, characterized in that the structural general formula of the organic electroluminescent compound is formula I:
in the formula (I), the compound is shown in the specification,
R1、R2、R5the substituted position is any substituted position on the benzene ring, and the number of the substituted positions is an integer of 0-4;
R3、R4the substituted position is any substituted position on the benzene ring, and the number of the substituted positions is an integer of 0-3;
R1-R5each independently is one of substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, a monocyclic or polycyclic C3-C30 aliphatic ring or aromatic ring connected to an adjacent substituent;
Ar1、Ar2each independently is one of substituted or unsubstituted C1-C30 alkyl, C2-C30 alkenyl, C2-C30 alkynyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-to 30-membered heteroaryl, substituted or unsubstituted 3-to 30-membered heteroarylamino, substituted or unsubstituted C6-C60 arylamino, C1-C30 alkoxy, C6-C60 aryloxy, C3-C30 aliphatic ring or 3-to 30-membered aromatic ring connected to adjacent substituents to form a mono-or polycyclic ring;
l is a bond, substituted or unsubstituted C6-C30 aryl.
2. The organic electroluminescent compound according to claim 1, wherein Ar is Ar1、Ar2Each independently is a substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted 3-to 26-membered heteroaryl; at least one carbon atom in the monocyclic or polycyclic C3-C30 aliphatic ring or 3-to 30-membered aromatic ring that is linked to an adjacent substituent is replaced or not replaced with a heteroatom.
3. The organic electroluminescent compound according to claim 2, wherein Ar is Ar1、Ar2Each independently is substituted or unsubstituted C10-C14 aryl, substituted or unsubstituted 18-to 22-membered heteroaryl; the heteroatom is one of nitrogen, oxygen or sulfur.
4. The organic electroluminescent compound according to claim 1, wherein L is benzene or deuterated benzene.
5. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is one of formula 1 to formula 107:
6. the method for producing an organic electroluminescent compound according to any one of claims 1 to 5, comprising the steps of:
dissolving the raw material 2 in THF, ventilating for three times, cooling to-70 to-80 deg.C, slowly adding N-BuLi, reacting for 1-3h, and reacting2Adding the raw material 1 under protection, slowly heating to 20-30 ℃, and stirring for 8-10h to prepare an intermediate 1;
adding the intermediate 1 into a reaction bottle, adding glacial acetic acid, heating to 60-80 ℃, and dropwise adding concentrated sulfuric acid to prepare an intermediate 2;
preparation of chemical formula 1
Adding the intermediate 2 and the raw material 3 into a mixed solution of toluene, ethanol and water, then ventilating for three times, adding a palladium catalyst and potassium carbonate under the protection of nitrogen, uniformly stirring, heating to 90-100 ℃, and reacting for 8-10 hours to prepare a chemical formula 1;
② preparation of chemical formula 2
Adding the intermediate 2 and the raw material 4 into a toluene solution, then ventilating for three times, adding a palladium catalyst, tri-tert-butylphosphine and sodium tert-butoxide under the protection of nitrogen, uniformly stirring, heating to 110 ℃, and reacting for 7-10h to obtain a chemical formula 2;
the synthetic route is as follows:
wherein R is1-R5、Ar1、Ar2And L is as defined above for formula I.
7. A hole transport layer in an organic electroluminescent device, wherein the hole transport layer in the organic electroluminescent device comprises the organic electroluminescent compound according to any one of claims 1 to 5 or the organic electroluminescent compound produced by the production method according to claim 6.
8. An organic electroluminescent device comprising the hole transport layer according to claim 7.
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| CN114702490A (en) * | 2022-05-06 | 2022-07-05 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound and preparation method thereof |
| CN116120319A (en) * | 2021-11-11 | 2023-05-16 | 奥来德(上海)光电材料科技有限公司 | Spiro organic electroluminescent compounds containing hetero atom, preparation method and application thereof |
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| CN112480115A (en) * | 2020-11-30 | 2021-03-12 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound containing nitrogen heterocycle and preparation method and application thereof |
| CN112500410A (en) * | 2020-11-30 | 2021-03-16 | 吉林奥来德光电材料股份有限公司 | Spiro nitrogen-containing organic luminescent compound, and preparation method and application thereof |
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| CN112079834A (en) * | 2020-09-18 | 2020-12-15 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound and application thereof |
| CN112480115A (en) * | 2020-11-30 | 2021-03-12 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound containing nitrogen heterocycle and preparation method and application thereof |
| CN112500410A (en) * | 2020-11-30 | 2021-03-16 | 吉林奥来德光电材料股份有限公司 | Spiro nitrogen-containing organic luminescent compound, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116120319A (en) * | 2021-11-11 | 2023-05-16 | 奥来德(上海)光电材料科技有限公司 | Spiro organic electroluminescent compounds containing hetero atom, preparation method and application thereof |
| CN114702490A (en) * | 2022-05-06 | 2022-07-05 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent compound and preparation method thereof |
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