CN113861041A - Compound and application thereof - Google Patents

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CN113861041A
CN113861041A CN202010622501.9A CN202010622501A CN113861041A CN 113861041 A CN113861041 A CN 113861041A CN 202010622501 A CN202010622501 A CN 202010622501A CN 113861041 A CN113861041 A CN 113861041A
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黄金华
张维宏
黄鑫鑫
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Beijing Eternal Material Technology Co Ltd
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Abstract

The invention relates to a compound and application thereof, wherein the compound has a structure shown in formula I, and a substituent L is introduced into 1-position of a naphthalene ring1‑Ar1Not only can adjust the steric hindrance of the 1-position, but also can effectively adjust and control the twist degree of the molecule so as to reduce the crystallinity of the molecule; secondly, the first step is to carry out the first,the group with a specific structure is introduced on the naphthalene ring 2-substituted N-atom and is matched with the naphthalene ring structure, so that the integral three-dimensional structure of the molecule can be effectively regulated and controlled, the accumulation density of the molecule is improved, and the refractive property of the molecule can be effectively improved, thereby further improving the performance of the device prepared by using the naphthalene ring. Especially, the effect of the material as an electron blocking layer is better, the luminous efficiency of the device can be improved, the driving voltage is reduced, and the service life is prolonged.

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
In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and crunchy optoelectronic products, with unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLEDs have been developed particularly rapidly, and have been commercially successful in the field of information display. The OLED can provide three colors of red, green and blue with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of colorful, light, thin and soft color and the like.
The core of the OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light.
People have developed various organic materials, and the organic materials are combined with various peculiar device structures, so that the carrier mobility can be improved, the carrier balance can be regulated and controlled, the electroluminescent efficiency can be broken through, and the attenuation of the device can be delayed. For quantum mechanical reasons, common fluorescent emitters mainly utilize singlet excitons generated when electrons and holes are combined to emit light, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet excitons and singlet excitons, which are called phosphorescent emitters, and the energy conversion efficiency can be increased by up to four times as compared with conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. Thermal excitation sensitized fluorescence (TASF) technology also achieves higher luminous efficiency by sensitizing the emitter by energy transfer using TADF-like materials.
As OLED products gradually enter the market, there are increasingly higher requirements on the performance of such products. The currently used OLED materials and device structures cannot completely solve the problems of OLED product efficiency, service life, cost and the like.
Therefore, there is a need in the art to develop an organic electroluminescent material that can improve the light emitting efficiency of the device, reduce the driving voltage, and prolong the lifetime.
Disclosure of Invention
An object of the present invention is to provide a compound which, when applied to an organic electroluminescent device, particularly as an electron blocking layer material, can further improve the luminous efficiency of the device, reduce the driving voltage, and prolong the service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I;
Figure BDA0002563496660000011
in the formula I, Ar is1And Ar2Each independently selected from one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
in the formula I, Ar is3One selected from the group consisting of halogen, carboxyl, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C1-C20 alkylcarbonyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
in the formula I, L is1And L2Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene;
in the formula I, L is3Any one selected from substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;
in the formula I, R is2Any one selected from hydrogen, halogen, carboxyl, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C1-C20 alkylcarbonyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
ar is1、Ar2、Ar3、L1、L2、L3And R2Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C20 alkylcarbonyl, carboxyl, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
The above "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from different substituents.
In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, for example, hydrogen (H) includes1H (protium, or written as H),2H (deuterium, or denoted as D), etc.; carbon (C) then comprises12C、13C and the like.
In the present invention, the heteroatom of heteroaryl is generally referred to as N, O, S.
In the present invention, the expression "-" denotes a loop structure, and indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can be bonded.
In the present invention, the C6-C60 aryl group includes C6-C60 monocyclic aryl group or C10-C60 fused ring aryl group, wherein monocyclic aryl group means that the aromatic ring exists as a single ring, no fusion exists, and includes, but is not limited to, phenyl, biphenyl, or terphenyl group; a fused ring aryl refers to a structure in which at least two aromatic rings are fused, including, but not limited to, naphthyl, anthryl, phenanthryl, fluorenyl, and the like.
In the present invention, the heteroaryl group of C3-C60 includes a monocyclic heteroaryl group of C3-C60 or a fused-ring heteroaryl group of C6-C30, wherein the monocyclic heteroaryl group means that the heteroaryl ring exists in the form of a single ring without fusion, including but not limited to pyridine, pyrimidine, triazine, or a group formed by connecting at least two thereof, etc.; fused heteroaryl refers to a fused ring aryl group containing a heteroatom, including but not limited to a dibenzofuran group, a dibenzothiophene group, or a carbazole group, and the like.
The C1-C20 chain alkyl group is preferably a C1-C10 chain alkyl group, more preferably a C1-C6 chain alkyl group, and examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-hexyl, n-octyl, n-pentyl, n-heptyl, n-nonyl, n-decyl and the like.
The above-mentioned C3-C20 cycloalkyl group is preferably cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
The above-mentioned C1-C12 alkoxy group is preferably methoxy; the above-mentioned C2-C12 alkenyl group is preferably vinyl; the above-mentioned C2-C12 alkynyl group is preferably ethynyl; the above-mentioned C1-C20 alkylcarbonyl group means R-CO-, wherein R represents C1-C20 alkyl.
The substituted or unsubstituted C6-C60 aryl group, preferably C6-C30 aryl group, is preferably selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthryl, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
Figure BDA0002563496660000021
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the above-mentionedThe anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
The substituted or unsubstituted C3-C60 heteroaryl group, preferably C3-C30 heteroaryl group, preferably the heteroaryl group is furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl or derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
In the present invention, the numbers for the substitution sites on the naphthalene ring are as follows:
Figure BDA0002563496660000031
in the structure of the compound of the invention, a substituent L is introduced into the 1-position of a naphthalene ring1-Ar1Not only can adjust the steric hindrance of the 1-position, but also can effectively adjust and control the twist degree of the molecule so as to reduce the crystallinity of the molecule; secondly, introducing into the 2-substituted N-atom of the naphthalene ring
Figure BDA0002563496660000032
The fragments are matched with a naphthalene ring structure, so that the integral three-dimensional structure of the molecule can be effectively regulated, the accumulation density of the molecule is improved, and the refractive property of the molecule can be effectively improved, so that the performance of a device prepared by using the fragments is further improved. Especially, the effect of the material as an electron blocking layer is better, the luminous efficiency of the device can be improved, the driving voltage is reduced, and the service life is prolonged.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Preferably, the compound has the structure shown in formula II;
Figure BDA0002563496660000033
in the formula II, Ar is1、Ar2、Ar3、L1、L2、L3And R2All having the same selection ranges as in formula I.
Preferably, the compound has the structure shown in formula III;
Figure BDA0002563496660000034
in the formula III, R is1Any one selected from hydrogen, halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
in the formula III, Ar is1、Ar2、Ar3、L1、L2And R2All having the same selection ranges as in formula I.
Preferably, the compound has the structure shown in formula IV;
Figure BDA0002563496660000041
in the formula IV, R is1And R3Each independently selected from any one of hydrogen, halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
in the formula IV, Ar is1、Ar2、L1、L2And R2All having the same selection ranges as in formula I.
The invention preferably introduces the naphthalene ring on the 2-substituted N-atom
Figure BDA0002563496660000042
The segment effectively improves the refractive property of the molecule to light by prolonging the axial conjugation of the molecule; and secondly, the introduction of 1,4 substituted segments of naphthalene ring enables the molecule to have better transmission capability and regulate and control the molecule stacking density to a certain degree, thereby further improving the performance of the device prepared by using the naphthalene ring.
Preferably, the compound has a structure represented by formula V;
Figure BDA0002563496660000043
in the formula II, Ar is1、Ar2、L1、L2、R1、R2And R3All having the same selection ranges as in formula IV.
Preferred embodiments of the invention
Figure BDA0002563496660000044
The site shown in the formula V is connected with the N atom, and compared with other connecting sites, the connecting molecule of the site has better light refraction performance and hole transmission performance, and the device performance can be further improved.
Preferably, Ar is1、Ar2And Ar3Each independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
Preferably, Ar is1Any one selected from the following substituted or unsubstituted groups:
Figure BDA0002563496660000051
wherein the wavy line mark represents the access bond of the group.
In the present invention, Ar having the above-mentioned specific structure is more preferred1Radicals, introduction of the above radicals, with naphthalene rings and
Figure BDA0002563496660000052
the cooperation can effectively adjust molecule HOMO, LUMO energy level and hole transmission ability, in addition, can also further improve the light refracting performance of material to further improve the device performance.
Preferably, Ar is2And Ar3Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9 dimethylfluorenyl, 9 diphenylfluorenyl, spirofluorenyl, triphenylene, fluoranthenyl, benzo 9,9 dimethylfluorenyl, benzospirofluorenyl.
Preferably, Ar is2And Ar3Each independently selected from any one of the following substituted or unsubstituted groups:
Figure BDA0002563496660000053
Figure BDA0002563496660000061
wherein the wavy line mark represents the access bond of the group.
In the present invention, Ar having the above-mentioned specific structure is more preferred2Radicals, introduction of the above radicals, with naphthalene rings and
Figure BDA0002563496660000062
and the energy levels of HOMO and LUMO of molecules and hole transmission capability can be adjusted by matching, so that the performance of the device is further improved.
Preferably, said L1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, preferably a single bond or a substituted or unsubstituted phenylene group.
Preferably, said L3Selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, and preferably substituted or unsubstituted phenylene.
Preferably, said R is1、R2And R3Each independently selected from hydrogen.
Preferably, the compound has any one of the structures shown as P1-P217.
The second purpose of the invention is to provide the application of the compound in the first purpose, and the compound is applied to an organic electroluminescent device.
Preferably, the compound is used as an electron blocking layer material in the organic electroluminescent device.
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 interposed between the first electrode and the second electrode, the organic layer containing at least one compound according to one of the objects.
Preferably, the organic layer includes an electron blocking layer containing a compound according to one of the objects.
The compound of the invention can be applied to organic electroluminescent devices, and can also be applied to other types of organic electronic devices, including organic field effect transistors, organic thin-film solar cells, information labels, electronic artificial skin sheets, sheet type scanners or electronic paper.
Specifically, another technical scheme 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 at least one of a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer and an electron transport layer, wherein the electron blocking layer contains at least one of the compounds.
The OLED includes first and second electrodes, 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 a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, 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 used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or 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 compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination 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 containing only one compound and a single layer containing a plurality of compounds. The hole transport region may have a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL) using the compound of formula I according to the present invention.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, 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), aromatic amine derivatives including compounds shown below as HT-1 to HT-51; or any combination thereof.
Figure BDA0002563496660000071
Figure BDA0002563496660000081
Figure BDA0002563496660000091
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 compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
Figure BDA0002563496660000101
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (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 single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked 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 emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
Figure BDA0002563496660000102
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, the combination of one or more of BFD-1 through BFD-24 listed below.
Figure BDA0002563496660000111
Figure BDA0002563496660000121
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light-emitting layer is selected from, but not limited to, one or more of PH-1 to PH-85.
Figure BDA0002563496660000122
Figure BDA0002563496660000131
Figure BDA0002563496660000141
Figure BDA0002563496660000151
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
Figure BDA0002563496660000161
Figure BDA0002563496660000171
Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
Figure BDA0002563496660000172
Figure BDA0002563496660000181
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1 to YPD-11 listed below.
Figure BDA0002563496660000182
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 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).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-65 listed below.
Figure BDA0002563496660000191
Figure BDA0002563496660000201
Figure BDA0002563496660000211
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following: LiQ, LiF, NaCl, CsF, Li2O、Cs2CO3BaO, Na, Li or Ca.
Compared with the prior art, the invention has the following beneficial effects:
in the structure of the compound of the invention, a substituent L is introduced into the 1-position of a naphthalene ring1-Ar1Not only can adjust the steric hindrance of the 1-position, but also can effectively adjust and control the twist degree of the molecule so as to reduce the crystallinity of the molecule; secondly, introducing into the 2-substituted N-atom of the naphthalene ring
Figure BDA0002563496660000221
The fragments are matched with a naphthalene ring structure, so that the integral three-dimensional structure of the molecule can be effectively regulated, the accumulation density of the molecule is improved, and the refractive property of the molecule can be effectively improved, so that the performance of a device prepared by using the fragments is further improved. Especially, the effect of the material as an electron blocking layer is better, the luminous efficiency of the device can be improved, the driving voltage is reduced, and the service life is prolonged.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
A representative synthetic route for the compounds of formula I of the present invention is as follows:
Figure BDA0002563496660000222
wherein Ar is1、Ar2、L1、L2、R1、R2And R3Are all the same as the symbols in formula I; pd2(dba)3Represents tris (dibenzylacetone) dipalladium (0), IPr. HCl represents 1, 3-bis (2, 6-diisopropylphenyl) imidurum chloride, NaOBu-t represents sodium tert-butoxide, (t-Bu)3P represents tri-tert-butylphosphine.
More specifically, the present invention provides a specific synthesis method of a representative compound as exemplified by the following synthesis examples, in which the solvents and reagents used in the following synthesis examples, such as 3-bromo-9, 9-dimethylfluorene, 1, bis (2, diisopropylphenyl) imidazolium chloride, tris (dibenzylacetone) dipalladium (0), toluene, methanol, ethanol, tri-tert-butylphosphine, potassium/sodium tert-butoxide, and other chemical reagents, are commercially available or custom-made from domestic chemical products, such as from the national pharmaceuticals group reagent company, Sigma-Aldrich company, chlorothalonil reagent company, and intermediates M1-M9, which are custom-made by the reagent company. In addition, they can be synthesized by a known method by those skilled in the art.
Synthesis example 1: synthesis of Compound P4
Figure BDA0002563496660000231
Into a 1000mL single-necked flask were charged 13.5g M1, 18g of 1- (4-bromophenyl) -4-phenylnaphthalene, and 0.9g of tris (dibenzylidene)Acetone based) dipalladium (i.e. Pd2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-1.
In a 1000mL single-neck bottle, 27g M1-1, 11.5g 2-bromo-biphenyl, 0.9g tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P4.
M/Z theoretical value: 699; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 700.
synthesis example 2: synthesis of Compound P10
Figure BDA0002563496660000232
In a 1000mL single-neck flask, 27g M1-1, 13.6g of 3-bromo-9, 9-dimethylfluorene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P10.
M/Z theoretical value: 739; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 740.
synthesis example 3: synthesis of Compound P15
Figure BDA0002563496660000233
In 1A000 mL single neck flask was charged with 27g M1-1, 16g of 2- (4-bromophenyl) dibenzofuran, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P15.
M/Z theoretical value: 789; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 790.
synthesis example 4: synthesis of Compound P16
Figure BDA0002563496660000241
Into a 1000mL single-neck flask were added 13.5g M1, 22.4g of 1- (4-bromophenyl) -4- (4-dibenzofuranyl) naphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-2.
Into a 1000mL single-necked flask were added 32.8g M1-2, 13.6g of 3-bromo-9, 9-dimethylfluorene, and 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P16.
M/Z theoretical value: 829; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 830.
synthesis example 5: synthesis of Compound P18
Figure BDA0002563496660000242
Into a 1000mL single-necked flask were added 13.5g M1, 20.4g of 1- (4-bromophenyl) -4- (2-naphthyl) naphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-3.
In a 1000mL single-neck flask, 30g M1-3, 13.6g of 2-bromo-9, 9-dimethylfluorene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P18.
M/Z theoretical value: 789; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 790.
synthesis example 6: synthesis of Compound P28
Figure BDA0002563496660000251
Into a 1000mL single-necked flask was added 13.5g M1, 18g of 1- (3-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-4.
In a 1000mL single-neck flask, 27g M1-4, 13.6g of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P28.
M/Z theoretical value: 739; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 740.
synthesis example 7: synthesis of Compound P53
Figure BDA0002563496660000252
In a 1000mL single-neck flask, 11g M2, 23.2g of 1- (4-bromophenyl) -4- (4-dibenzothienyl) naphthalene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M2-1.
In a 1000mL single-neck flask, 27g M2-1, 13g of 3-bromo-dibenzothiophene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P53.
M/Z theoretical value: 785; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 786.
synthesis example 8: synthesis of Compound P79
Figure BDA0002563496660000253
In a 1000mL single-neck flask, 15g M3, 18g of 1- (4-bromobenzene) were addedPhenyl-4-naphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M3-1.
In a 1000mL single-neck flask, 28.5g M3-1, 13.6g of 3-bromo-9, 9-dimethylfluorene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and filtering to obtain light yellow powder P79.
M/Z theoretical value: 765 (5); ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 766.
synthesis example 9: synthesis of Compound P109
Figure BDA0002563496660000261
In a 1000mL single-neck flask, 16.5g M4, 18g of 1- (4-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M4-1.
In a 1000mL single-neck bottle, 30.5g M4-1, 8g bromobenzene, 0.9g tris (dibenzylideneacetone) dipalladium (i.e., Pd) was added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction solution, concentrating the organic phase, and adding AThe alcohol was stirred for 1h and suction filtered to give a pale yellow powder P109.
M/Z theoretical value: 689; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 690.
synthesis example 10: synthesis of Compound P151
Figure BDA0002563496660000262
In a 1000mL single-neck flask, 15g M5, 36g of 1- (4-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. And cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P151.
M/Z theoretical value: 865; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 866.
synthesis example 11: synthesis of Compound P176
Figure BDA0002563496660000271
In a 1000mL single-neck flask, 15g M6, 16g of 1- (4-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M6-1.
In a 1000mL single-necked flask, 29.5g M6-1, 13.6g of 3-bromo-9, 9-dimethylfluorene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. After the reaction is finished, the reaction is stoppedAnd (4) reacting. And cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P176.
M/Z theoretical value: 779; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 780.
synthesis example 12: synthesis of Compound P184
Figure BDA0002563496660000272
In a 1000mL single-neck flask, 16.2g M7, 18g of 1- (4-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M7-1.
In a 1000mL single-neck flask, 30g M7-1, 15.4g of 4-bromoterphenyl, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. And cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P184.
M/Z theoretical value: 831; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 832.
synthesis example 13: synthesis of Compound P195
Figure BDA0002563496660000281
In a 1000mL single-neck flask, 16.2g M8, 18g of 1- (4-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr. HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), evacuatedChanging nitrogen for 3 times, and heating the reaction to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M8-1.
In a 1000mL single-neck flask, 30g M8-1, 16g of 2- (4-bromophenyl) dibenzofuran, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. And cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P195.
M/Z theoretical value: 845; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 846.
synthesis example 14: synthesis of Compound P197
Figure BDA0002563496660000282
In a 1000mL single-neck flask, 16.2g M7, 18g of 1- (3-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M7-2.
In a 1000mL single-neck flask, 30g M7-2, 8g bromobenzene, 0.9g tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P197.
M/Z theoretical value: 679; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 680.
synthesis example 15: synthesis of Compound P214
Figure BDA0002563496660000291
In a 1000mL single-neck flask, 16.2g M9, 18g of 1- (3-bromophenyl) -4-phenylnaphthalene, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M9-1.
In a 1000mL single-neck flask, 30g M9-1, 12g of 2-bromobiphenyl, 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd) were added2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. And cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P214.
M/Z theoretical value: 755; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 756.
synthesis example 16: synthesis of Compound P215
Figure BDA0002563496660000292
Into a 1000mL single-necked flask were added 13.5g M1, 20g of 1- (4-bromonaphthyl) -4-phenylnaphthalene, and 0.9g of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5g IPr.HCl, 500mL toluene, 14.4g sodium tert-butoxide (NaOBu-t), vacuumized and nitrogen exchanged for 3 times, and the reaction is heated to 90 ℃ for 5 hours. And stopping the reaction after the reaction is finished. Cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder M1-5.
At 10A00 mL single neck flask was charged with 30g M1-5, 13.6g of 3-bromo-9, 9-dimethylfluorene, 0.9g (1mmol) of tris (dibenzylideneacetone) dipalladium (i.e., Pd)2(dba)3) 0.5mL of tri-tert-butylphosphine ((t-Bu)3P), 500mL of toluene and 14.4g of sodium tert-butoxide (NaOBu-t), vacuumizing and changing nitrogen for 3 times, and heating the reaction to 110 ℃ for 5 hours. And stopping the reaction after the reaction is finished. And cooling to room temperature, separating the reaction liquid, concentrating the organic phase, adding methanol, stirring for 1h, and performing suction filtration to obtain light yellow powder P215.
M/Z theoretical value: 789; ZAB-HS type mass spectrometer (manufactured by Micromass, UK) M/Z measured value: 790.
example 1
The embodiment provides an organic electroluminescent device, which is specifically prepared as follows:
the glass plate coated with the ITO transparent conductive layer (as anode) was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to less than 1 × 10-5Pa, performing vacuum evaporation on the anode layer film to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm;
and (3) evaporating the compound P4 on the hole transport layer in vacuum to be used as an electron barrier layer material of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 80 nm.
A luminescent layer of the device is evaporated on the electron blocking layer in vacuum, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material PH-59 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, the evaporation rate of the dye RPD-8 is set to be 3% of the main material in proportion, and the total evaporation film thickness is 30 nm;
and (3) carrying out vacuum evaporation on an electron transport layer of the device on the light-emitting layer, adjusting the ratio of the material ET-46: ET-57(50/50, w/w), evaporation rate of 0.1nm/s, total film thickness of 30 nm;
LiF with the thickness of 0.5nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 150nm is used as a cathode of the device.
The organic electroluminescent devices provided in examples 2 to 16 and comparative examples 1 to 4 were fabricated in the same manner as in example 1, except that the compound P4 as an electron blocking layer material was replaced with the compounds shown in table 1.
The structure of the electron barrier material of the comparative example is as follows:
Figure BDA0002563496660000301
wherein R-1 and R-2 are described in detail in patent application CN110511151A, R-3 is described in patent application KR1020190101739A, and R-4 is described in patent application JP 2008174647A.
And (3) performance testing:
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement: the current efficiencies of the organic electroluminescent devices prepared in examples 1 to 16 and comparative examples 1 to 4 were measured at the same luminance using a digital source meter (Keithley2400) and a luminance meter (ST-86LA type luminance meter, photoelectric instrument factory, university of beijing). Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 3000cd/m2Then, the ratio of the brightness to the current density at this time was measured as the current efficiency, and the test results are shown in table 1.
TABLE 1
Figure BDA0002563496660000302
Figure BDA0002563496660000311
As can be seen from the data in Table 1, the compounds of the present invention are useful in organic electroluminescenceWhen the electron barrier material of the optical device is used, the brightness of the device reaches 3000cd/m2The current efficiency is as high as more than 19.8cd/A, even more than 21cd/A, the current efficiency can be effectively improved, and the material is an electronic barrier layer material with good performance.
The compound R-1 of comparative example 1 is different from the compound P10 of example 2 in that the compound R-1 has a structure having one fewer benzene ring in the axial direction than P10 (i.e., Ar in the present invention)3) When the compound is used as an electron barrier material of an organic electroluminescent device, the current efficiency is 19.5 cd/A. The current efficiency of this compound is inferior to that of P10, since P10 has a higher refractive index than R-1, which is more favorable for light extraction.
In comparison with the compound of the present invention, in the compound R-2 of comparative example 2, terphenyl and 3-spirofluorene are bonded to N, respectively; in comparison with the compound R-3 of the comparative example 3 and the compound of the present invention, R-3 is a phenanthrene derivative; in comparison with the compound of the present invention, R-4 of comparative example 4 has a naphthyl group substituted naphthyl group and a perylene group attached to N. The data show that none of the devices of comparative examples 2-4 performed as well as the examples.
Thus, it is found that the compound of the present invention has a naphthalene ring having N at the 2-position
Figure BDA0002563496660000312
The substitution is an important factor for enabling the compound to be applied to an organic electroluminescent device to bring excellent performance.
By comparing example 2 with example 4, it can be seen that when Ar is used3In the case of phenyl (i.e., the structure shown in formula IV) (example 2), the light-emitting effect of the device can be further improved compared to the compound substituted with other groups (example 4), probably because the introduction of dibenzofuran in P16 not only changes the HOMO and LUMO energy levels of the molecule, but also distorts the molecular spatial structure to some extent, thereby reducing the hole transport capability between molecules, but the present invention solves this problem by selecting phenyl to substitute on naphthalene ring.
By comparing example 2 with example 16, it can be seen that when L is3In the case of phenylene (i.e., the structure of formula III), as compared to the other linking groups (example 1)6) The luminous efficiency of the device can be further improved, because the introduction of the naphthalene ring in P215 causes large rigid distortion in the molecule, the distortion changes the space conformation of the molecule and further influences the hole transmission capability of the molecule, and the problem is solved by adopting phenylene connection.
By comparing example 2 with example 6, it can be seen that
Figure BDA0002563496660000313
Compared with the P-substitution of N atom (P10 in example 2), the P-substitution of N atom (P28 in example 6) can further improve the light-emitting efficiency of the device, mainly because the molecules have better light refraction performance and hole transmission performance due to the meta-connection.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.

Claims (13)

1. A compound having a structure according to formula I;
Figure FDA0002563496650000011
in the formula I, Ar is1And Ar2Each independently selected from one of substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
in the formula I, Ar is3Selected from halogen, carboxyl, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted COne of substituted C1-C20 alkylcarbonyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
in the formula I, L is1And L2Each independently selected from any one of a single bond, a substituted or unsubstituted C6-C60 arylene, a substituted or unsubstituted C3-C60 heteroarylene;
in the formula I, L is3Any one selected from substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C3-C60 heteroarylene;
in the formula I, R is2Any one selected from hydrogen, halogen, carboxyl, cyano, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C1-C12 alkoxy, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C1-C20 alkylcarbonyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
ar is1、Ar2、Ar3、L1、L2、L3And R2Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C1-C20 alkylcarbonyl, carboxyl, cyano, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl.
2. The compound of claim 1, wherein the compound has a structure represented by formula II;
Figure FDA0002563496650000021
in the formula II, Ar is1、Ar2、Ar3、L1、L2、L3And R2All having the same limitations as in formula I.
3. The compound of claim 1, wherein the compound has a structure according to formula III;
Figure FDA0002563496650000022
in the formula III, R is1Any one selected from hydrogen, halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
in the formula III, Ar is1、Ar2、Ar3、L1、L2And R2All having the same limitations as in formula I.
4. The compound of claim 1, wherein the compound has a structure according to formula IV;
Figure FDA0002563496650000031
in the formula IV, R is1And R3Each independently selected from any one of hydrogen, halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl and C3-C30 heteroaryl;
in the formula IV, Ar is1、Ar2、L1、L2And R2All having the same limitations as in formula I.
5. The compound of claim 4, wherein the compound has a structure represented by formula V;
Figure FDA0002563496650000032
in the formula V, Ar1、Ar2、L1、L2、R1、R2And R3All having the same limitations as in formula IV.
6. A compound according to any one of claims 1 to 3 wherein Ar is1、Ar2And Ar3Each independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl.
7. The compound of any one of claims 1-5, wherein Ar is Ar1Any one selected from the following substituted or unsubstituted groups:
Figure FDA0002563496650000041
wherein the wavy line mark represents the access bond of the group.
8. A compound according to any one of claims 1 to 3 wherein Ar is2And Ar3Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthracyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, 9 dimethylfluorenyl, 9 diphenylfluorenyl, spirofluorenyl, triphenylene, fluoranthenyl, benzo 9,9 dimethylfluorenyl, benzospirofluorenyl;
preferably, Ar is2And Ar3Each independently selected from any one of the following substituted or unsubstituted groups:
Figure FDA0002563496650000042
Figure FDA0002563496650000051
wherein the wavy line mark represents the access bond of the group.
9. The compound of claim 1 or 2, wherein L is1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene group, a substituted or unsubstituted C3-C30 heteroarylene group, preferably a single bond or a substituted or unsubstituted phenylene group;
preferably, said L3Any one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, and preferably substituted or unsubstituted phenylene.
10. A compound according to claim 4 or 5, wherein R is1、R2And R3Each independently selected from hydrogen.
11. The compound of claim 1, wherein the compound has any one of the following structures P1-P217:
Figure FDA0002563496650000061
Figure FDA0002563496650000071
Figure FDA0002563496650000081
Figure FDA0002563496650000091
Figure FDA0002563496650000101
Figure FDA0002563496650000111
Figure FDA0002563496650000121
Figure FDA0002563496650000131
Figure FDA0002563496650000141
Figure FDA0002563496650000151
Figure FDA0002563496650000161
Figure FDA0002563496650000171
Figure FDA0002563496650000181
Figure FDA0002563496650000191
Figure FDA0002563496650000201
Figure FDA0002563496650000211
Figure FDA0002563496650000221
Figure FDA0002563496650000231
Figure FDA0002563496650000241
Figure FDA0002563496650000251
Figure FDA0002563496650000261
Figure FDA0002563496650000271
Figure FDA0002563496650000281
Figure FDA0002563496650000291
12. use of a compound according to any one of claims 1 to 11 in an organic electroluminescent device;
preferably, the compound is used as an electron blocking layer material in the organic electroluminescent device.
13. An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, the organic layer containing at least one compound according to any one of claims 1 to 11;
preferably, the organic layer comprises an electron blocking layer containing the compound according to any one of claims 1 to 11.
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