CN113527302B - Compound and application thereof - Google Patents

Compound and application thereof Download PDF

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CN113527302B
CN113527302B CN202010294126.XA CN202010294126A CN113527302B CN 113527302 B CN113527302 B CN 113527302B CN 202010294126 A CN202010294126 A CN 202010294126A CN 113527302 B CN113527302 B CN 113527302B
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CN113527302A (en
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孙恩涛
方仁杰
刘叔尧
吴俊宇
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Beijing Eternal Material Technology Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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    • Y02E10/00—Energy generation through renewable energy sources
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  • Electroluminescent Light Sources (AREA)

Abstract

The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula (1), the compound takes quinazoline and triazole as an electron-deficient group, cyano groups are introduced into the triazole through bridging, and fluorene or spirofluorene and derivative groups thereof are introduced into a six-membered pyrimidine ring, so that the obtained novel electron-transporting material has a relatively proper molecular dipole moment and can be in more compact contact with other organic layers in the process of forming the device, and therefore, when the compound is used as the electron-transporting layer material in an organic electroluminescent device, the electron injection and migration efficiency in the device can be effectively improved, and the excellent effects of high luminous efficiency, low starting voltage and long service life of the device are ensured.

Description

Compound and application thereof
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
An organic electroluminescent (OLED: organic Light Emission Diodes) device is a device with a sandwich-like structure, comprising positive and negative electrode layers and an organic functional material layer sandwiched between the electrode layers. And applying voltage to the electrode of the OLED device, injecting positive charges from the positive electrode, injecting negative charges from the negative electrode, and transferring and meeting the positive charges and the negative charges in the organic layer to emit light compositely under the action of an electric field. Because the OLED device has the advantages of high brightness, quick response, wide viewing angle, simple process, flexibility and the like, the OLED device has a great deal of attention in the novel display technical field and the novel illumination technical field. At present, the technology is widely applied to display panels of products such as novel illumination lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with rapid development and high technical requirements.
With the continuous advancement of the OLED in the two fields of illumination and display, the research on the core materials of the OLED is also more focused. This is because an efficient, long-life OLED device is typically the result of an optimized match of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functionalized materials of various structures. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like.
The OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life of the device is prepared, the performance of the OLED device is improved continuously, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be researched and innovated continuously so as to prepare the functional material with higher performance. Based on this, the OLED materials community has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
In order to further meet the demand for the continuous improvement of the photoelectric performance of OLED devices and the demand for energy saving of mobile electronic devices, there is a continuous need to develop new and efficient OLED materials, where the development of new electron transport materials with high electron injection capability and high mobility is of great importance.
Disclosure of Invention
It is an object of the present invention to provide a compound having high electron injection capability and high mobility, which can be used as an electron transport material for an OLED device, achieving low starting voltage and high luminous efficiency of the device.
To achieve the purpose, the invention adopts the following technical scheme:
The present invention provides a compound having a structure represented by formula (1);
In the formula (1), n is an integer of 0 to 4, for example, 1,2, 3, etc., m is an integer of 0 to 7, for example, 1,2, 3, 4, 5, 6, etc., and r is 0 or 1;
when R is 0, it means that X is not present, i.e., R 3 and R 4 are two independent groups, linked to the parent nucleus by a single bond; when R is 1, R 3 and R 4 are linked by X;
In the formula (1), R 1 and R 2 are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
In the formula (1), R 3 and R 4 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
according to common knowledge in the art, when either of R 3 and R 4 is selected from hydrogen or deuterium, R 3 and R 4 cannot be connected, i.e. R is 0;
In the formula (1), L 1 and L 2 are each independently selected from any one of a single bond, a substituted or unsubstituted C1-C12 chain alkylene group, a substituted or unsubstituted C1-C12 alkyleneoxy group, a substituted or unsubstituted C3-C12 cycloalkylene group, a substituted or unsubstituted C6-C60 arylene group, and a substituted or unsubstituted C3-C60 heteroarylene group;
In the formula (1), X is selected from single bond, O, S, NR 5 or CR 6R7,R5-R7 and is independently selected from any one of hydrogen, deuterium, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R 1-R7、X、L1 and L 2 are each independently selected from one or a combination of at least two of halogen, cyano, nitro, hydroxy, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused ring heteroaryl. The foregoing groups refer to the selection range of substituents when the "substituted or unsubstituted" group has substituents, and the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the substituents are plural, they may be selected from different substituents, and the same meaning is given in the present invention when the same expression mode is referred to, and the selection ranges of the substituents are not described in detail herein.
The compound of the general formula of the invention takes quinazoline and triazole as an electron-deficient group, cyano groups are introduced into the triazole through bridging, and fluorene or spirofluorene and derivative groups thereof are introduced into six-membered pyrimidine ringsThe obtained novel electron transport material has more proper molecular dipole moment, and can be in more compact contact with other organic layers in the process of forming a device, so that molecules have good electron injection and migration performances, therefore, when the compound disclosed by the invention is used as an electron transport layer material in an organic electroluminescent device, the electron injection and migration efficiency in the device can be effectively improved, and the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
In the present invention, the heteroatom of the heteroaryl group is generally selected from N, O, S.
In the present invention, the expression "ring structure" means that the linking site is located at any position on the ring structure that can be bonded.
In the present invention, the C6-C60 (arylene) group is preferably a C6-C30 (arylene) group, and the C3-C60 (arylene) heteroaryl group is preferably a C3-C30 (arylene) heteroaryl group.
In the invention, the carbon number of the C1-C12 chain alkyl and the C1-C10 chain alkyl can be C2, C3, C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C3-C12 cycloalkyl and the C3-C10 cycloalkyl can be C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C1-C12 alkoxy, C1-C10 alkoxy and C1-C10 thioalkoxy can be C2, C3, C4, C5, C6, C7, C8, C9, C10 and the like; the carbon number of the C6-C60 aryl group can be C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, C32, C34, C36, C38, C40, C42, C46, C48, C50, C52, C54, C56, C58, etc.; the carbon number of the C3-C60 heteroaryl group can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, C32, C34, C36, C38, C40, C42, C46, C48, C50, C52, C54, C56, C58, etc.; the carbon number of the C6-C30 arylamino group can be C8, C10, C12, C14, C16, C18, C20, C26, C28, etc.; the carbon number of the C3-C30 heteroaryl amino group can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C6-C30 aryl and the C6-C30 monocyclic aryl can be C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C10-C30 condensed ring aryl group can be C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C3-C30 heteroaryl and the C3-C30 monocyclic heteroaryl can be C3, C4, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like; the carbon number of the C6-C30 fused ring heteroaryl group can be C8, C10, C12, C14, C16, C18, C20, C26, C28 and the like. The number of carbons is merely illustrative and is not limited to the above.
Preferably, the compound has a structure represented by formula (1-1) or formula (1-2);
In the formula (1-1), m, n, R 1-R4、L1 and L 2 all have the same meaning as in the formula (1);
In the formula (1-2), p and q are each independently an integer of 0 to 4, for example, 1,2, 3, etc.;
In the formula (1-2), R 8 and R 9 are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, and the C6-C30 aryl or C3-C30 heteroaryl is connected with the benzene ring in the formula (1-2) in a single bond or in a condensed form; "attached in fused form" refers to a connection in which two aromatic or heteroaromatic rings share two carbons, e.g., a benzene ring and a benzene ring are attached in fused form to form a naphthalene ring;
in the formula (1-2), X, m, n, R 1、R2、L1 and L 2 each have the same meaning as in the formula (1).
Preferably, in the formula (1-2), the R 8 and R 9 are each independently selected from any one of C1-C10 chain alkyl, C6-C30 aryl or C3-C30 heteroaryl, preferably any one of methyl, tert-butyl, phenyl or benzofuranyl, and the phenyl or benzofuranyl is connected to the benzene ring in the formula (1-2) in a single bond or in a condensed form.
Preferably, each of R 1 and R 2 is independently selected from any one of substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably any one of methyl, ethyl, isopropyl, furyl, thienyl or phenyl.
Preferably, each of R 3 and R 4 is independently selected from any one of substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably substituted or unsubstituted C1-C12 chain alkyl or substituted or unsubstituted C6-C60 aryl, preferably methyl or phenyl.
Preferably, each R 5-R7 is independently selected from any one of substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, preferably substituted or unsubstituted C1-C12 chain alkyl or substituted or unsubstituted C6-C60 aryl, further preferably methyl or phenyl.
Preferably, the L 1 and L 2 are each independently selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene, preferably a single bond or a substituted or unsubstituted C6-C60 arylene, further preferably any one of a single bond, phenylene, biphenylene, or terphenylene.
Preferably, the L 1 is selected from a substituted or unsubstituted C6-C60 arylene or a substituted or unsubstituted C3-C60 heteroarylene, preferably any of phenylene, biphenylene or terphenylene.
Preferably, X is a single bond.
According to the invention, fluorene or spirofluorene groups are preferably introduced on the six-membered pyrimidine ring, so that the compound has more proper molecular dipole moment, and when the compound is applied to an OLED device, the luminous efficiency of the device can be further improved, and the starting voltage can be reduced.
Preferably, the compound has a structure represented by formula (1-3) or formula (1-4);
Both m, n, p, q, R 1、R2、L1、L2、R8 and R 9 have the same meaning as in formulae (1-1) and (1-2).
Preferably, the compound has any one of the structures shown in C1 to C95:
It is a second object of the present invention to provide the use of a compound according to one of the objects, which is applied to an organic electroluminescent device.
In addition to organic electroluminescent devices, the compounds of the invention may also be used in other organic electronic devices, including optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners, or electronic papers.
Preferably, the compound is used as an electron transport material of an organic electroluminescent device.
The compound of the present invention has a high electron affinity and thus a high electron accepting ability, and is suitable for use as an electron transport material, but is not limited thereto.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer between the first electrode and the second electrode, the organic layer comprising at least one compound according to one of the objects.
The OLED device prepared by the compound has low starting voltage and high luminous efficiency, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
Preferably, the organic layer comprises an electron transport layer comprising at least one compound of one of the purposes.
Specifically, an embodiment of the present invention provides an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transmission layer, a light-emitting layer and an electron transmission layer, wherein the hole injection layer is formed on the anode layer, the hole transmission layer is formed on the hole injection layer, the cathode layer is formed on the electron transmission layer, and the light-emitting layer is arranged between the hole transmission layer and the electron transmission layer; wherein the electron transport layer contains the compound of the general formula of the present invention represented by the above formula (1).
More specifically, the organic electroluminescent device will be described in detail.
The OLED device includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), and aromatic amine derivatives as shown below in HT-1 to HT-34; or any combination thereof.
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The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI-1 through HI-3 described below; one or more compounds of HT-1 through HT-34 may also be used to dope one or more compounds of HI-1 through HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-12 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of YPD-1 through YPD-11 listed below.
The organic electroluminescent device of the present invention includes an electron transport region between a light emitting layer and a cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed by applying the compound of the present invention to a multi-layer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-57 listed below.
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The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following:
Liq、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
compared with the prior art, the invention has the following beneficial effects:
According to the general formula compound disclosed by the invention, quinazoline and triazole are used as an electron-deficient group, cyano groups are introduced into triazole through bridging, fluorene or spirofluorene and derivative groups thereof are introduced into six-membered pyrimidine rings, and the obtained novel electron-transporting material has a relatively proper molecular dipole moment, and can be in more compact contact with other organic layers in the process of forming a device, so that molecules have good electron injection and migration performances, and the device has relatively high current efficiency and relatively low driving voltage. Therefore, when the compound of the present invention is used as an electron transport layer material in an organic electroluminescent device, electron injection and migration efficiency in the device can be effectively improved, thereby ensuring excellent effects of high luminous efficiency and low starting voltage of the device.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The representative synthetic route for the compounds of formula (1) of the present invention is as follows:
Firstly, taking substituted or unsubstituted 2, 4-dichloroquinazoline as a raw material, and synthesizing an intermediate M-1 by nucleophilic substitution reaction with hydrazine hydrate under the alkaline condition of triethylamine; the second step of the intermediate M-1 is subjected to condensation reaction with various aldehydes to generate an intermediate M-2; step three, the intermediate M-2 is oxidized and cyclized under the action of iodobenzene acetate to synthesize an intermediate M-3; and fourthly, performing Suzuki coupling reaction on the intermediate M-3 and various boric acids to generate target products, wherein n, M, r, R 1-R4、L1、L2 and X have the same meaning as in the formula (1), and PhI (OAc) 2 is iodobenzene acetate.
Illustratively, the following synthesis examples provide synthesis procedures for specific compounds using various chemicals such as ethyl acetate, ethanol, sodium sulfate, toluene, tetrahydrofuran, methylene chloride, acetic acid, potassium carbonate, etc., as basic chemical raw materials, all purchased from Shanghai Taitan technologies and Cheng Chemicals Co. The mass spectrometer used for determining the following compounds was ZAB-HS type mass spectrometer measurement (manufactured by Micromass Co., UK).
Synthesis example 1:
Synthesis of Compound C6
(1) Preparation of Compound 1-1
After 2, 4-dichloroquinazoline (500 g,2.5 mol) was dissolved in 10L of ethanol in a flask, hydrazine hydrate (470 g,7.5mol,80% aqueous solution) was added dropwise under stirring at 5℃while maintaining the temperature below 10 ℃. After the dropping, naturally raising the temperature to room temperature for reaction for 1 hour, filtering the separated solid, washing the solid with water and ethanol respectively, and airing to obtain an off-white solid compound 1-1 (415 g, 86%).
(2) Preparation of Compounds 1-2
Compound 1-1 (200 g,1.03 mol) was added to a flask containing 2L of ethanol, p-cyanobenzaldehyde (120 g,1.13 mol) was added dropwise with stirring at room temperature, the stirring reaction was continued for 30 minutes after the addition, the resulting solid was filtered, rinsed with ethanol and n-hexane, respectively, and dried to give compound 1-2 (190 g, 60%) as a yellow solid.
(3) Preparation of Compounds 1-3
Compounds 1-2 (184 g,600 mmol) were added to a flask containing 4L ethanol and iodobenzene acetate (232 g,720 mmol) was added in portions with stirring at room temperature, after which the reaction was continued with stirring for 1.5 hours and TLC showed complete reaction. After stirring for 5 minutes with 4L of n-hexane, the precipitated solid was suction-filtered, rinsed with n-hexane and dried to give compound 1-3 (119 g, 65%) as a pale brown yellow solid.
(4) Preparation of Compound C6
Compounds 1-3 (4.9 g,18 mmol), 1-boronic acid-9, 9-spirobifluorene (6.5 g,18 mmol) and potassium carbonate (7.45 g,54 mmol) were added to a solution containing tetrahydrofuran: in a flask of water (150 mL:30 mL), nitrogen was replaced with stirring at room temperature, and [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride (Pd (dppf) Cl 2, 128mg,0.18 mmol) was added. After the addition was completed, the reaction was heated under reflux with stirring under nitrogen for 12 hours, and TLC showed complete reaction. The white solid precipitated was filtered. Dissolving with dichloromethane, drying over anhydrous sodium sulfate, and column chromatography (eluent dichloromethane) afforded compound C6 (7.9 g, 75% yield) as a white solid. Calculated molecular weight: 585.20 found C/Z585.2.
Synthesis example 2:
synthesis of Compound C33
(1) Preparation of Compound 2-1
Compounds 1-3 (30.5 g,0.1 mol), 3-chloro-phenylboronic acid (15.6 g,0.1 mol), potassium carbonate (41 g,0.3 mol), pd (dppf) Cl 2 (732 mg,1 mmol) were added to a flask containing 400mL/100mL tetrahydrofuran/water, nitrogen was replaced and the reaction was heated at reflux under nitrogen for 10 hours, and TLC showed completion of the reaction. Cooling to room temperature, separating, extracting the water phase with ethyl acetate, mixing the organic phases, drying over anhydrous sodium sulfate, and separating and purifying by column chromatography to obtain compound 2-1 (26 g, 67%).
(2) Preparation of Compound C33
2-1 (6.9 G,18 mmol), 2-boronic acid-9, 9-spirobifluorene (6.5 g,18 mmol), potassium carbonate (7.45 g,54 mmol), dibenzylideneacetone dipalladium (Pd 2(dba)3, 367mg,0.4 mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (Sphos, 328mg,0.8 mmol) were added to a flask containing 1, 4-dioxane/water 150mL/15mL, the nitrogen was replaced and the reaction was heated under reflux for 24 hours under nitrogen atmosphere, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C33 (10.2 g, yield 86%). Calculated molecular weight: 661.23, found C/Z:661.2.
Synthesis example 3:
synthesis of Compound C51
(1) Preparation of Compound 3-1
The compound 2-boronic acid-9, 9-dimethylfluorene (23.8 g,0.1 mol), 3-chloro-phenylboronic acid (15.6 g,0.1 mol), potassium carbonate (41 g,0.3 mol) and tetrakis (triphenylphosphine) palladium (Pd (PPh 3)4, 1.15g,1 mmol) were added to a flask containing 300mL/100mL/100mL of toluene/ethanol/water, nitrogen was replaced and the reaction was heated under reflux for 6 hours under nitrogen atmosphere, TLC showed complete reaction, cooled to room temperature, the separated liquid, the aqueous phase was extracted with ethyl acetate, the organic phase was combined, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 3-1 (26.7 g, 88%).
(2) Preparation of Compound 3-2
Compound 3-1 (24.3 g,80 mmol), pinacol diboronate (30.5 g,120 mmol) and potassium acetate (23.5 g,240 mmol) were added to a flask containing 1, 4-dioxane (500 mL), and palladium acetate (180 mg,0.8 mmol), SPhos (1 g,2.4 mmol) was added after displacing nitrogen with stirring at room temperature. After the addition was completed, the reaction was stirred at reflux for 12 hours and TLC monitored for the end of the reaction. The 1, 4-dioxane was removed by rotary evaporation, water and methylene chloride were added to the mixture, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 3-2 (26.3 g, yield 83%).
(3) Preparation of Compound C51
Compound 3-2 (7.1 g,18 mmol), compound 2-1 (6.8 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd2 (dba) 3 (367 mg,0.4 mmol), sphos (328 mg,0.8 mmol) were added to a flask containing 1, 4-dioxane/150 mL/15mL of water, nitrogen was replaced and the reaction was heated under reflux under nitrogen for 24 hours, and TLC showed completion. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C51 (9.1 g, yield 82%). Calculated molecular weight: 615.24, found C/Z:615.2.
Synthesis example 4:
Synthesis of Compound C64
(1) Preparation of Compound 4-1
Compound 1-1 (200 g,1.03 mol) was added to a flask containing 2L of ethanol, p-chlorobenzaldehyde (158 g,1.13 mol) was added dropwise with stirring at room temperature, the reaction was continued with stirring for 20 minutes after the addition, the resulting solid was filtered, rinsed with ethanol and n-hexane, respectively, and dried to give compound 4-1 (205 g, 63%) as a yellow solid.
(2) Preparation of Compound 4-2
Compound 4-1 (190 g,600 mmol) was added to a flask containing 4L of ethanol, iodobenzene acetate (232 g,720 mmol) was added in portions with stirring at room temperature, and after the addition was complete, stirring was continued for 2 hours, and TLC showed completion of the reaction. The precipitated solid was suction-filtered, rinsed with n-hexane and dried to give compound 4-2 (122 g, 65%) as a pale brown yellow solid.
(3) Preparation of Compound C4-3
Compound 4-2 (31.4 g,100 mmol), 2-boronic acid-9, 9-spirobifluorene (36 g,100 mmol), potassium carbonate (41.4 g,300 mmol), pd (dppf) Cl 2 (731 mg,1 mmol) were added to a flask containing 1L tetrahydrofuran and 200mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 8 hours, and TLC showed complete reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound 4-3 (39.2 g, yield 66%).
(4) Preparation of Compound C64
Compound 4-3 (10.7 g,18 mmol), 4-cyanobenzylboronic acid (2.6 g,18 mmol), potassium carbonate (7.45 g,54 mmol) and Pd (PPh 3)4 (208 mg,0.18 mmol) were added to a flask containing toluene/ethanol/water 100mL/20mL/20mL, nitrogen was replaced and the reaction was heated under reflux for 6 hours under nitrogen atmosphere, TLC showed complete reaction, the precipitated solid was filtered, rinsed with water and ethanol, respectively, and after drying, column chromatography was separated and purified to give compound C64 (10.3 g, yield 87%). Calculated molecular weight: 661.23, found C/Z:661.2.
Synthesis example 5:
synthesis of Compound C77
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(1) Preparation of Compound 5-1
Compound 1-1 (200 g,1.03 mol) was added to a flask containing 2L of ethanol, 3-cyanobenzaldehyde (120 g,1.13 mol) was added dropwise with stirring at room temperature, the reaction was continued with stirring for 30 minutes after the addition, the resulting solid was filtered, rinsed with ethanol and n-hexane, respectively, and dried to give compound 5-1 (193 g, 61%) as a yellow solid.
(2) Preparation of Compound 5-2
Compound 5-1 (184 g,600 mmol) was added to a flask containing 4L of ethanol, iodobenzene acetate (232 g,720 mmol) was added in portions with stirring at room temperature, and after the addition was complete, stirring was continued for 1.5 hours, and TLC showed complete reaction. The precipitated solid was suction-filtered, rinsed with n-hexane and dried to give compound 5-2 (115 g, 63%) as a pale brown yellow solid.
(3) Preparation of Compound C77
Compound 5-2 (4.9 g,18 mmol), 1-boronic acid-9, 9-spirobifluorene (6.5 g,18 mmol) and potassium carbonate (7.45 g,54 mmol) were added to a solution containing tetrahydrofuran: in a flask of water (150 mL:30 mL), pd (dppf) Cl 2 (128 mg,0.18 mmol) was added after nitrogen was replaced with stirring at room temperature. After the addition was completed, the reaction was heated under reflux with stirring under nitrogen for 20 hours, and TLC showed complete reaction. The white solid precipitated was filtered. Dissolving with dichloromethane, drying over anhydrous sodium sulfate, and column chromatography (eluent dichloromethane) afforded compound C77 (7.4 g, 70% yield) as a white solid. Calculated molecular weight: 585.20 found C/Z585.2.
Example 1
The embodiment provides a preparation method of an organic electroluminescent device, which specifically comprises the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
Placing the glass substrate with the anode in a vacuum cavity, vacuumizing until the pressure is less than 10 -5 Pa, vacuum evaporating HI-3 on the anode layer film by using a multi-source co-evaporation method as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
Vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a first hole transport layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40nm;
vacuum evaporating HT-14 on the first hole transport layer to obtain a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 10nm;
Vacuum evaporating a luminescent layer of the device on the second hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of the dye BFD-4 is set to be 5% in proportion, and the total film thickness of evaporation is 20nm;
vacuum evaporating ET-17 on the luminescent layer as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 5nm;
Evaporating compounds C6 and ET-57 on the hole blocking layer by utilizing a multi-source co-evaporation method as an electron transmission layer, regulating the evaporation rate of the compound C6 to be 0.1nm/s and setting the ratio of the evaporation rate of the compound C6 to the evaporation rate of the ET-57 to be 100% (the evaporation rate of the compound C6 and the evaporation rate of the ET-57 to be 1:1), and ensuring the total evaporation film thickness to be 23nm;
LiF with the thickness of 1nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 80nm serves as a cathode of the device.
Examples 2-17 differ from example 1 only in the replacement of compound C6 with other compounds, see in particular table 1.
Comparative example 1
The difference from example 1 is that compound C6 is replaced by compound D-1 (WO 2019206242A 1).
Comparative example 2
The difference from example 1 is that compound C6 was replaced with compound D-2 (CN 109824672A).
Comparative example 3
The difference from example 1 is that compound C6 was replaced with compound D-3 (CN 109824672A).
Comparative example 4
The difference from example 1 is that compound C6 was replaced with compound D-4 (CN 109824672A).
Comparative example 5
The difference from example 1 is that compound C6 was replaced with compound D-5 (CN 109824672A).
Comparative example 6
The difference from example 1 is that compound C6 is replaced by compound D-6 (CN 109824672A).
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Performance test:
The driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples were measured using a Photo Research company PR 750 type optical radiometer, an ST-86LA type luminance meter (university of Beijing photoelectric instrumentation Co., ltd.) and a Keithley4200 test system at the same luminance. Specifically, the voltage was raised at a rate of 0.1V per second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent device reached 1000cd/m 2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency.
The results of the performance test are shown in Table 1.
TABLE 1
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As can be seen from Table 1, in the case that other materials are the same in the structure of the organic electroluminescent device, the organic electroluminescent device provided by the embodiment of the invention has higher current efficiency, lower driving voltage and longer service life, wherein the current efficiency is 9.65-10.19cd/A, and the driving voltage is 3.63-3.83V.
The compound D-1 was different from the compound C6 only in that the substituted triazine group was used instead of the spirofluorene group, and the remaining structures were the same, and in comparative example 1, D-1 was used as an electron transport material, the driving voltage of the device was 3.91V, the current efficiency was 9.10cd/A, and it was inferior to the device of example 1.
The difference between the compound D-2 and the compound C51 is that the substituted anthracene group is adopted to replace fluorenyl group, the rest structures are the same, the D-2 is adopted as an electron transport material in the comparative example 2, the driving voltage of the device is 4.02V, the current efficiency is 8.79cd/A, and the performance is slightly poorer than that of the device in the embodiment 3.
Based on the comparison result, the reason is presumed that the compound of the invention adopts a mode of connecting quinazoline and triazole with fluorene or spirofluorene and derivative groups thereof to form new molecules, and the molecular structure of the invention has more proper molecular dipole moment than D-1 and D-2 as an electron transmission material, thereby being more beneficial to electron injection. On the other hand, the introduction of fluorene or spirofluorene groups enables the molecules to be more compact in contact with other organic layers after vapor deposition on the device, so that the electron mobility is better improved.
Compound D-3 differs from compound C95 only in that it does not contain a cyano group, and comparative example 3 uses D-3 as an electron transporting material, the driving voltage of the device is 4.23V, the current efficiency is 8.11cd/A, and the effect is deteriorated as compared with example 6. It is proved that the introduction of cyano group in the compound provided by the invention plays a crucial role in improving the performance of the device.
The compounds D-4 to D-6 were free of cyano groups and fluorene or spirofluorene and its derivative groups, and the devices of comparative examples 4 to 6 were higher in driving voltage, lower in current efficiency and inferior in device performance as compared with the examples.
In summary, the compound provided by the invention can have higher electron injection and migration performance by introducing cyano groups through bridging on triazole and introducing fluorene or spirofluorene and derivative groups thereof on six-membered pyrimidine ring, so that the device has higher current efficiency and lower driving voltage, and two conditions are indispensable.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.

Claims (21)

1. A compound characterized by having a structure represented by formula (1);
In the formula (1), n is an integer of 0 to 2, m is an integer of 0 to 4, and r is 0 or 1;
In the formula (1), R 1 and R 2 are each independently selected from any one of deuterium, halogen, cyano, C1-C12 chain alkyl, C1-C12 alkoxy, C3-C12 cycloalkyl, C6-C30 aryl and C3-C30 heteroaryl;
In the formula (1), R 3 and R 4 are each independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
In the formula (1), L 1 is selected from any one of substituted or unsubstituted C6-C30 arylene;
In the formula (1), L 2 is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene;
in the formula (1), X is selected from single bond, O, S, NR 5 or CR 6R7,R5-R7 and is independently selected from any one of hydrogen, deuterium, C1-C12 chain alkyl, C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
R 1-R7、X、L1 and L 2 are each independently selected from one or a combination of at least two of halogen, cyano, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 monocyclic aryl, C10-C30 fused ring aryl, C3-C30 monocyclic heteroaryl, C6-C30 fused ring heteroaryl.
2. The compound according to claim 1, wherein the compound has a structure represented by formula (1-1) or formula (1-2);
in the formula (1-1), m, n, R 1-R4、L1 and L 2 all have the same defined range as claim 1;
In the formula (1-2), p and q are each independently integers of 0 to 4;
In the formula (1-2), R 8 and R 9 are each independently selected from any one of deuterium, halogen, cyano, nitro, hydroxyl, C1-C10 chain alkyl, C1-C10 alkoxy, C3-C10 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, and the C6-C30 aryl or C3-C30 heteroaryl is connected with the benzene ring in the formula (1-2) in a single bond or in a condensed form;
In the formula (1-2), X, m, n, R 1、R2、L1 and L 2 each have the same definition as in claim 1.
3. The compound according to claim 2, wherein in the formula (1-2), each of R 8 and R 9 is independently selected from any one of C1-C10 chain alkyl, C6-C30 aryl, or C3-C30 heteroaryl.
4. The compound according to claim 2, wherein in the formula (1-2), the R 8 and R 9 are each independently selected from any one of methyl, tert-butyl, phenyl or benzofuranyl, and the phenyl or benzofuranyl is connected to the benzene ring in the formula (1-2) in a single bond form or in a condensed form.
5. A compound according to any one of claims 1 to 3, wherein R 1 and R 2 are each independently selected from any one of C1-C12 chain alkyl, C6-C30 aryl, C3-C30 heteroaryl.
6. The compound of claim 5, wherein R 1 and R 2 are each independently selected from any one of methyl, ethyl, isopropyl, furyl, thienyl, or phenyl.
7. The compound of claim 1 or 2, wherein R 3 and R 4 are each independently selected from any one of substituted or unsubstituted C1-C12 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
8. The compound of claim 7, wherein R 3 and R 4 are each independently selected from substituted or unsubstituted C1-C12 chain alkyl or substituted or unsubstituted C6-C30 aryl.
9. The compound of claim 8, wherein R 3 and R 4 are each independently selected from methyl or phenyl.
10. The compound of claim 1 or 2, wherein each R 5-R7 is independently selected from any one of C1-C12 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
11. The compound of claim 10, wherein each R 5-R7 is independently selected from C1-C12 chain alkyl or substituted or unsubstituted C6-C30 aryl.
12. The compound of claim 11, wherein each R 5-R7 is independently selected from methyl or phenyl.
13. A compound according to any one of claims 1 to 3, wherein L 2 is selected from any one of a single bond, phenylene, biphenylene or terphenylene.
14. A compound according to any one of claims 1 to 3, wherein L 1 is selected from any one of phenylene, biphenylene or terphenylene.
15. A compound according to claim 1 or 2, wherein X is a single bond.
16. The compound according to claim 2, wherein the compound has a structure represented by formula (1-3) or formula (1-4);
both m, n, p, q, R 1、R2、L1、L2、R8 and R 9 have the same defined ranges as in claim 2.
17. The compound of claim 1, wherein the compound has any one of the structures shown below:
18. Use of a compound according to any one of claims 1 to 17, wherein the compound is used in an organic electroluminescent device.
19. The use according to claim 18, wherein the compound is used as an electron transport material for an organic electroluminescent device.
20. An organic electroluminescent device, characterized in that it comprises a first electrode, a second electrode and at least one organic layer located between the first electrode and the second electrode, the organic layer comprising at least one compound according to any one of claims 1 to 17.
21. The organic electroluminescent device of claim 20, wherein the organic layer comprises an electron transport layer comprising at least one compound of any one of claims 1 to 17.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109037446A (en) * 2017-11-23 2018-12-18 北京鼎材科技有限公司 Compound and its application in field of organic electroluminescence
CN109824671A (en) * 2017-11-23 2019-05-31 北京鼎材科技有限公司 A kind of quinazo triazole derivatives and its application in field of organic electroluminescence
WO2019206242A1 (en) * 2018-04-27 2019-10-31 北京鼎材科技有限公司 Organic electroluminescent material and device

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109037446A (en) * 2017-11-23 2018-12-18 北京鼎材科技有限公司 Compound and its application in field of organic electroluminescence
CN109824671A (en) * 2017-11-23 2019-05-31 北京鼎材科技有限公司 A kind of quinazo triazole derivatives and its application in field of organic electroluminescence
WO2019206242A1 (en) * 2018-04-27 2019-10-31 北京鼎材科技有限公司 Organic electroluminescent material and device

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