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CN116199676B - Compound and application thereof, and organic electroluminescent device containing compound - Google Patents

Compound and application thereof, and organic electroluminescent device containing compound Download PDF

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CN116199676B
CN116199676B CN202310054214.6A CN202310054214A CN116199676B CN 116199676 B CN116199676 B CN 116199676B CN 202310054214 A CN202310054214 A CN 202310054214A CN 116199676 B CN116199676 B CN 116199676B
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CN116199676A (en
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贾刚刚
丁兴立
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Beijing Tuofan Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

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Abstract

The invention relates to the field of organic electroluminescence, and discloses a compound and application thereof, and an organic electroluminescent device containing the compound, wherein the compound is a compound containing a structural formula 1, and triazine and derivative groups thereof and quinazoline and two electron-deficient groups of derivative groups thereof are simultaneously introduced into the compound. The invention solves the problem that the starting voltage of the device is increased due to the electron transport material with lower electron mobility, thereby influencing the power efficiency.

Description

Compound and application thereof, and organic electroluminescent device containing compound
Technical Field
The invention relates to the field of organic electroluminescence, in particular to a compound and application thereof, and an organic electroluminescent device containing the compound.
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.
In order to prepare the OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life of the device, the performance of the OLED device is continuously improved, 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 continuously researched and innovated so as to prepare the functional material with higher performance. Based on this, the OLED material community has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better service life of the device, but currently used electron transport materials have yet to be optimized, especially the electron mobility and electron injection capability thereof are not high, which on one hand can lead to a decrease in the probability of recombination of holes and electrons due to unbalanced injection and transport of carriers, thereby decreasing the luminous efficiency of the device, and on the other hand, electron transport materials with lower electron mobility can lead to an increase in the starting voltage of the device, thereby affecting the power efficiency and unfavorably saving energy. CN111747932 a discloses a compound containing triazine and quinazoline groups, but the performance of such materials is still to be improved, and more kinds of high-performance electron transport materials are to be developed.
Accordingly, there is a need in the art to develop a novel electron transport material having higher electron injection capability and electron mobility and an OLED device having higher luminous efficiency and lower starting voltage.
Disclosure of Invention
In order to solve the technical problems, the invention provides a compound, application thereof and an organic electroluminescent device containing the compound.
The invention adopts the following specific scheme: a compound represented by the following chemical formula 1:
chemical formula 1:
wherein R1, R2, R3 and R4 are each independently selected from one of a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
Ar is selected from one of H, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
ar1 and Ar2 are each independently selected from Ar;
When substituents are present on the above groups, each of the substituents is independently selected from one of cyano, halogen, C1-C10 alkanyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic or fused-ring aromatic hydrocarbon group, C3-C30 monocyclic or fused-ring heteroaromatic hydrocarbon group.
Ar1 and Ar2 groups of the compound represented by the chemical formula 1 are selected from a compound A-1, and the chemical formula of the compound A-1 is as follows:
Chemical formula A-1:
Wherein X is selected from O or S; any SP 2 hybridized carbon atom on A-1 participates in bond formation.
At least one of Ar1 and Ar2 groups of the compound represented by the chemical formula 1 is selected from the compound A-1.
The compound is selected from the following structures:
Wherein R1, R2, R3 and R4 are each independently selected from one of a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; ar and Ar2 are selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; x is selected from O or sulfur; when substituents are present on the above groups, each of the substituents is independently selected from one of halogen, C1-C10 alkanyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic or fused ring aromatic hydrocarbon group, C3-C30 monocyclic or fused ring heteroaromatic hydrocarbon group.
The compound is selected from the following structures:
Wherein R1, R2, R3 and R4 are each independently selected from one of a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; ar and Ar2 are selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; ar3 is selected from one of halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; x is selected from O or sulfur; when substituents are present on the above groups, each of the substituents is independently selected from one of halogen, C1-C10 alkanyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic or fused ring aromatic hydrocarbon group, C3-C30 monocyclic or fused ring heteroaromatic hydrocarbon group.
The compound is selected from the following structures:
Wherein R1, R2, R3 and R4 are all hydrogen atoms, ar is selected from phenyl, ar2 is selected from benzene, biphenyl, naphthalene, triphenylene, fluoranthene, fluorene, indenofluorene, spirofluorene or combination of two or more of benzene, biphenyl, naphthalene, triphenylene, fluoranthene, fluorene, indenofluorene and spirofluorene, and SP 3 hybridized carbon atoms in Ar2 can be substituted by C1-C6 alkyl and C6-C12 aryl.
The compound is selected from any one of the following structures 1-48:
the oxygen atoms in the compounds are replaced by other atoms.
The present invention provides an application of a compound, wherein the compound represented by the chemical formula 1 is used as an electron transport material or a red light host material in an organic electroluminescent device.
The invention provides an organic electroluminescent device, which comprises a substrate, wherein an anode layer, a plurality of luminous functional layers and a cathode layer are 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 or the light emitting layer contains any one or a combination of at least two of the compounds represented by chemical formula 1.
Compared with the prior art, the invention has the following beneficial effects:
The invention provides a compound and application thereof, and an organic electroluminescent device containing the compound, wherein triazine and derivative groups thereof and quinazoline and derivative groups thereof are simultaneously introduced into the compound containing the structural formula 1, and biphenyl with a specific substitution form connects the two groups, meanwhile, the biphenyl is limited to have no substituent, and the special connection mode is matched with the respective electron deficiency characteristics of the triazine and the quinazoline, so that the compound is more beneficial to electron injection and migration compared with the prior art, and the compound has high electron injection capacity and high electron migration capacity, and can effectively improve the electron injection and migration efficiency in the device when being used for an electron transport layer material in the organic electroluminescent device, thereby ensuring that the device obtains excellent effects of high luminous efficiency and low starting voltage.
Detailed Description
The present invention will be described below with reference to specific examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the description is only illustrative and is not intended to limit the scope of the invention. In addition, in the following description, descriptions of well-known structures and techniques are omitted so as not to unnecessarily obscure the present invention.
The present invention is a compound represented by the following chemical formula 1:
chemical formula 1:
wherein R1, R2, R3 and R4 are each independently selected from one of a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group;
Ar is selected from one of H, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
ar1 and Ar2 are each independently selected from Ar;
When substituents are present on the above groups, each of the substituents is independently selected from one of cyano, halogen, C1-C10 alkanyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic or fused-ring aromatic hydrocarbon group, C3-C30 monocyclic or fused-ring heteroaromatic hydrocarbon group.
Ar1 and Ar2 groups of the compound represented by the chemical formula 1 are selected from a compound A-1, and the chemical formula of the compound A-1 is as follows:
Chemical formula A-1:
Wherein X is selected from O or S; any SP 2 hybridized carbon atom on A-1 participates in bond formation.
At least one of Ar1 and Ar2 groups of the compound represented by the chemical formula 1 is selected from the compound A-1.
The Ar group of the compound represented by the chemical formula 1 is selected from one of substituted or unsubstituted C6-C10 alkyl, substituted or unsubstituted C6-C16 aryl and substituted or unsubstituted C6-C12 heteroaryl.
The compounds of the present invention contain the following structure:
Wherein R1, R2, R3 and R4 are each independently selected from one of a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; ar and Ar2 are selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; x is selected from O or sulfur; when substituents are present on the above groups, each of the substituents is independently selected from one of halogen, C1-C10 alkanyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic or fused ring aromatic hydrocarbon group, C3-C30 monocyclic or fused ring heteroaromatic hydrocarbon group.
The compounds of the present invention contain the following structure:
Wherein R1, R2, R3 and R4 are each independently selected from one of a hydrogen atom, a deuterium atom, a halogen, a cyano group, a substituted or unsubstituted C1-C12 alkyl group, a substituted or unsubstituted C6-C30 aryl group and a substituted or unsubstituted C3-C30 heteroaryl group; ar and Ar2 are selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; ar3 is selected from one of halogen, cyano, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; x is selected from O or sulfur; when substituents are present on the above groups, each of the substituents is independently selected from one of halogen, C1-C10 alkanyl or cycloalkyl, C2-C10 alkenyl, C1-C6 alkoxy or thioalkoxy, C6-C30 monocyclic or fused ring aromatic hydrocarbon group, C3-C30 monocyclic or fused ring heteroaromatic hydrocarbon group.
The compounds of the present invention contain the following structure:
Wherein R1, R2, R3 and R4 are all hydrogen atoms, ar is selected from phenyl, ar2 is selected from benzene, biphenyl, naphthalene, triphenylene, fluoranthene, fluorene, indenofluorene, spirofluorene or combination of two or more of benzene, biphenyl, naphthalene, triphenylene, fluoranthene, fluorene, indenofluorene and spirofluorene, and SP 3 hybridized carbon atoms in Ar2 can be substituted by C1-C6 alkyl and C6-C12 aryl.
Further, the compound of the present invention is selected from one of the following compounds 1 to 48.
Among the structures of the above-listed specific compounds, structures in which O atoms are replaced with other atoms are also within the scope of the present disclosure.
The compound disclosed by the invention is simultaneously introduced with triazine and derivative groups thereof and quinazoline and derivative groups thereof, and the two groups are connected by biphenyl in a specific substitution form, and meanwhile, no substituent is arranged on the biphenyl, and the special connection mode is matched with the respective electron deficiency characteristics of the triazine and the quinazoline, so that the compound disclosed by the invention is more beneficial to electron injection and migration compared with the prior art, and the compound has high electron injection capacity and high electron migration capacity, and can effectively improve the electron injection and migration efficiency in the device when being used for an electron transport layer material in an organic electroluminescent device, thereby ensuring that the device obtains excellent effects of high luminous efficiency and low starting voltage.
On the other hand, substituents (R1, R2, R3 and R4) on triazine and quinazoline groups in the compound provided by the invention are all connected with a mother nucleus through single bonds, and the substituents cannot be mutually fused or fused with the mother nucleus.
The compound has higher electron affinity and thus stronger electron accepting capability, is suitable for being used as an electron transmission material in an organic electroluminescent device, and can be applied to the technical fields of 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, large-area sensors such as sheet scanners, electronic papers and the like.
In another aspect, the present invention provides the use of the compound containing the compound of formula 1 as an electron transport material or a red host material in an organic electroluminescent device.
The invention provides an organic electroluminescent device, which comprises a substrate, a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains any one or at least two of the compounds of one of the purposes; the organic electroluminescent device comprises a substrate, an anode layer, a plurality of luminous functional layers and a cathode layer, wherein the anode layer, the luminous functional layers and the cathode layer are 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 or the light emitting layer contains any one or a combination of at least two of the compounds of chemical formula 1.
In one embodiment, 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 injection layer is located between the anode layer and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds.
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.
The luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material, etc. 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.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the 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 containing chemical formula 1 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 an Electron Injection Layer (EIL), electron Transport Layer (ETL), hole Blocking Layer (HBL) device, and 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, one or more combinations of the following: liq, liF, naCl, csF, li 2O、Cs2CO3, baO, na, li, ca. The formation method for forming each layer described above may be, for example, vapor deposition, sputtering, solution coating, or the like, using a conventional formation method.
Example 1
Synthesis of Compound 1:
(1) Preparation of Compound 1-1
1-0 (47.8 G,100 mmol) of raw material, 3-chlorobenzoic acid (15.6 g,100 mmol), potassium carbonate (41.4 g,300 mmol) and tetraphenylpalladium phosphate (1.15 g,1 mmol) were added under nitrogen protection, 300mL of toluene, 100mL of ethanol and 60mL of water were added, and the mixture was reacted at 110℃under nitrogen protection overnight. Solid is separated out in the reaction process. Thin Layer Chromatography (TLC) detects the completion of the reaction of the starting materials, stops the reaction, cools to room temperature, filters the precipitated solid, and rinses with water and ethanol, respectively, and dries. The target compound 1-1 (weight 39.1 g) was obtained.
M/z calculated: 509.13, ZAB-HS Mass Spectrometry (manufactured by Micromass Co., UK) found m/z 509.13.
(2) Preparation of Compounds 1-2
Compound 1-1 (40.8 g,0.08 mol), pinacol diboronate (30.5 g,0.12 mol) and potassium acetate (24 g,0.24 mol) were charged into a flask containing 1, 4-dioxane (300 mL), and Pd 2(dba)3 (733 mg,0.8 mmol) and Sphos (CAS: 657408-07-6) (1 g) were added after displacing nitrogen with stirring at room temperature. After the addition was completed, the reaction was stirred at reflux for 24 hours and TLC monitored for the end of the reaction. And (3) filtering the precipitated solid after cooling. Washing with water and drying gave compound 1-2 (weight 28.7 g).
(3) Preparation of Compound C1
Compounds 1-2 (10.39 g,20 mmol) and 2-chloro-4-phenylquinazoline (4.8 g,20 mmol) were added to a three-necked flask, then potassium carbonate (8.3 g,60 mmol) was dissolved in 60mL of water and added to the three-necked flask, 250mL of tetrahydrofuran was added, and [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride (146 mg,0.2 mmol) was further added to displace nitrogen 3 times, and the oil bath was heated to 80℃for 6 hours, and TLC monitored the end of the reaction. Cooling the reaction solution to room temperature, extracting with dichloromethane, mixing organic phases, drying, and concentrating; silica gel column chromatography, elution with a mixed solvent of 5 volumes of petroleum ether and 0.6 volumes of dichloromethane, gave compound 1 as a white solid (mass 9.6 g). m/z calculated: 679.24, ZAB-HS type Mass Spectrometry (manufactured by Micromass Co., UK) found m/z 679.24.
Example 2
Synthesis of Compound S-1:
Referring to the synthesis of compound 1 in example 1, S-1 was obtained by changing the starting material shown in 1-0 to the starting material shown in S-1-0. m/z calculated: 695.21 measured m/z of ZAB-HS type mass spectrometer 695.21.
Example 3
Synthesis of Compound 20:
The specific synthesis procedure differs from that of preparation 1 in that starting material 1-0 was replaced by starting material 20-0 in an equivalent amount to give compound 20 as a white solid, calculated m/z:769.25 measured m/z of ZAB-HS type Mass Spectrometry unit 769.25
Example 4
Synthesis of Compound 22
(1) Preparation of Compound 22-1
1000 Ml of a three-port bottle, nitrogen protection, 800 ml of tetrahydrofuran, 6.80 g (10 mmol) of a compound shown in a formula 1, heating and dissolving, stirring and cooling to-20 ℃, slowly dropwise adding 11 ml of a lithium diisopropylamide tetrahydrofuran solution with the concentration of 1.0M, keeping the temperature at-20 ℃ for 1 hour, adding 5g of 1, 2-dibromoethane at one time, slowly heating to 25 ℃ for 2 hours, adding water and stirring, filtering the separated solid, drying the solid, separating by a silica gel column chromatography, eluting with a mixed solvent of 20 volumes of petroleum ether and 0.5 volumes of dichloromethane, and obtaining the compound 22-1 as a white solid with the mass of 1.3 g.
M/z calculated: 759.15, 757.15, ZAB-HS Mass Spectrometry m/z 759.15, 757.15.
The nuclear magnetic data of compound 22-1 are as follows:
1H-NMR (Bruker, switzerland, 300MHz Nuclear magnetic resonance spectrometer) ,D6-DMSO),δ8.31(m,2H),δ8.11(m,1H),δ8.09(m,1H),δ8.00～7.89(m,6H),δ7.84～7.77(m,3H),δ7.70～7.45(m,11H),δ7.39(m,1H),δ7.23(m,2H),δ7.09(m,1H).
(2) Preparation of Compound 22
Reference compound 1-1 was prepared, except that 3-chlorobenzoic acid was replaced with phenylboric acid in an equal amount, and the compound shown as 1-0 was replaced with compound 22-1 in an equal amount, to give compound 22 as a white solid.
M/z calculated: 755.27, measured m/z of ZAB-HS mass spectrometer 755.27.
Example 5
Synthesis of Compound 42
250 Ml three-neck oil bath heating, adding 7.59 g (10 mmol) of the compound shown in formula 22-1, 1.8 g (20 mmol) of CuCN,30 ml of DMSO,0.2 g of O-rphyrin, heating to 160 ℃ for reaction for 48 hours, cooling, adding water, filtering the obtained solid, and extracting the obtained solid with hot toluene to obtain a crude toluene solution. After concentrating the dry toluene, separating by silica gel column chromatography, eluting with a mixed solvent of 10 volumes of petroleum ether and 1 volume of dichloromethane, to obtain compound 42 as a white solid, with a mass of 5.1 g.
M/z calculated: 704.23, ZAB-HS Mass Spectrometry m/z 704.23.
Example 6
Synthesis of Compound D1:
reference compound 1 was prepared with the difference that 3-chlorobenzoic acid was replaced with an equal amount of 4-chlorobenzoic acid to give compound D1 as a white solid.
M/z calculated: 679.24, ZAB-HS type Mass Spectrometry m/z 679.24.
The following are examples of organic electroluminescent devices, and the structures of the compounds used in the process of preparing the organic electroluminescent devices are as follows:
Example 7
The embodiment provides an organic electroluminescent device, which is prepared by the following steps:
(1) Ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in a mixed solvent of acetone and ethanol, baking in a clean environment until water is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam;
(2) Placing the glass substrate with the anode in a vacuum cavity, vacuumizing until the pressure is less than 10 < -5 > Pa, and regulating the evaporation rate of a hole transport material HT-28 to be 0.1nm/s and the evaporation rate of a hole injection material HI-2 to be 0.007nm/s by using a multi-source co-evaporation method on the anode layer film, wherein the total evaporation film thickness is 10nm, so as to form a hole injection layer;
(3) Vacuum evaporating HT-28 on the hole injection layer as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 40nm;
(4) Vacuum evaporating HT-32 on the first hole transport layer to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 10nm;
(5) 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, the evaporation rate of the dye BFD-10 is regulated to be 0.005nm/s, and the total evaporation film thickness is 20nm by utilizing a multi-source co-evaporation method;
(6) 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;
(7) Evaporating an electron transport material on the hole blocking layer, and adjusting the evaporation rate of the compound 1 to 0.1nm/, wherein the total film thickness of evaporation is 25nm;
(8) LiF with the thickness of 1nm is evaporated in vacuum on the electron transport layer to serve as an electron injection layer, and finally an Al layer with the thickness of 80nm is evaporated to serve as a cathode of the device.
Example 8
The difference from example 1 is that compound 1 is replaced with compound 4.
Example 9
The difference from example 1 is that compound 1 is replaced with compound 6.
Example 10
The difference from example 1 is that compound 1 is replaced with compound 14.
Example 11
The difference from example 1 is that compound 1 is replaced with compound 17.
Example 12
The difference from example 1 is that compound 1 is replaced with compound 22.
Example 13
The difference from example 1 is that compound 1 is replaced with compound 24.
Example 14
The difference from example 1 is that compound 1 is replaced with compound 32.
Example 15
The difference from example 1 is that compound 1 is replaced with compound 42.
Example 16
The difference from example 1 is that compound 1 is replaced with compound S-1.
Comparative example 1
The difference from example 1 is that compound 1 is replaced by compound C1.
Comparative example 2
The difference from example 1 is that compound 1 is replaced with compound D1.
Performance testing
(1) 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 ST-86LA type luminance meter (university of Beijing photoelectric instrumentation Co.) and 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/m2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency.
(2) The lifetime test of LT95 is as follows: the time in hours for the luminance of the organic electroluminescent device to drop to 1425cd/m2 was measured using a luminance meter maintaining a constant current at a luminance of 1500cd/m 2.
The test results are shown in Table 1.
TABLE 1
The results prove that when the compound provided by the invention is used as an electron transport material of an OLED device, the luminous efficiency of the device can be improved, the starting voltage can be reduced, and the service life can be prolonged. The compound containing the chemical formula 1 is more beneficial to electron injection and migration, so that the compound has both high electron injection capability and high electron migration capability, and when being used as an electron transport layer material in an organic electroluminescent device, the compound can effectively improve the electron injection and migration efficiency in the device, thereby ensuring that the device has excellent effects of high luminous efficiency and low starting voltage, and simultaneously prolonging the service life of the device and having high stability.
The foregoing description is only one specific embodiment of the present invention, but the specific protection scope of the present invention is not limited to the foregoing description, and any simple substitution or modification within the scope of the technical idea disclosed in the present invention and according to the technical scheme of the present invention should be within the protection scope of the present invention.

Claims (4)

1. A compound, characterized in that the compound is selected from the following structures:
；
wherein R1, R2, R3 and R4 are each independently selected from a hydrogen atom, a deuterium atom and an unsubstituted C1-C12 alkyl group; ar and Ar2 are selected from unsubstituted C6-C30 aryl; ar3 is selected from cyano, unsubstituted C6-C30 aryl; x is selected from O or sulfur.
2. A compound characterized by any of the following structures:
；
；
。
3. Use of a compound according to claims 1-2 as an electron transporting material or red host material in an organic electroluminescent device.
4. An organic electroluminescent device is characterized by comprising a substrate, wherein an anode layer, a plurality of luminous functional layers and a cathode layer are 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 or the light emitting layer contains any one or a combination of at least two of the compounds according to claims 1-2.
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