CN114805089A - Compound and application thereof - Google Patents

Compound and application thereof Download PDF

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CN114805089A
CN114805089A CN202110064215.XA CN202110064215A CN114805089A CN 114805089 A CN114805089 A CN 114805089A CN 202110064215 A CN202110064215 A CN 202110064215A CN 114805089 A CN114805089 A CN 114805089A
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李之洋
高文正
黄金华
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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 a formula I, a bisarylamine structure is substituted on a specific site of the compound provided by the invention, and the bisarylamine structure is matched with a specific aryl group, so that the compound has good hole injection and transmission performance, and can be applied to an organic electroluminescent device, effectively improve the efficiency of the device, reduce the driving voltage and prolong the service life, and particularly has the best effect when being used as a hole transmission layer material.

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 been rapidly developed and are the hot spot of research in the field. 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 multilayer 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.
Conventional fluorescent emitters emit light mainly by using singlet excitons generated when electrons and holes are combined, and are still widely used in 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-based materials.
The hole transport material has obvious influence on the voltage of the device, regulates and controls the transport balance of carriers in the device, improves the carrier mobility of the hole transport material, can improve the luminous efficiency and delay the attenuation of the device. Although the products adopting the OLED display technology are commercialized at present, the lifetime, efficiency, and other properties of the device are continuously improved to meet the pursuit of higher quality.
Therefore, there is a need in the art to develop a wider variety of organic materials for organic electroluminescent devices, such that the devices have higher light emitting efficiency, lower driving voltage and longer service life.
Disclosure of Invention
An object of the present invention is to provide a compound, and more particularly, to provide a hole transport material, which can improve luminous efficiency and lifespan, and reduce driving voltage when applied to an OLED device.
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 BDA0002903741900000011
in the formula I, A is selected from substituted or unsubstituted C10-C50 aryl;
in the formula I, Ar is 1 、Ar 2 、Ar 3 And Ar 4 Each independently selected from any one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
in the A, the substituted groups are respectively and independently selected from any one or at least two combinations of amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C30 arylamino and C6-C30 aryl;
ar is 1 、Ar 2 、Ar 3 And Ar 4 Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C30 arylamino, C6-C30 aryl, C3-C30 heteroaryl and C3-C30 heteroarylamino.
The compound provided by the invention contains a diarylamine structure, the position of the diarylamine is respectively located at the critical position and the para position of the aromatic ring A, the critical arylamine fixes partial structure of molecules due to the influence of steric hindrance, so that the molecules cannot rotate freely, the crystallization of a transmission material on a device is prevented, and proper structural distortion can be favorable for blocking excitons; the para-aromatic amine and the aryl system in the mother nucleus structurally form a plane structure beneficial to transmission, and under the combined action of the para-aromatic amine and the aryl system, the compound provided by the invention has the excellent characteristics of low voltage, high efficiency and long service life when being used in an OLED device, and particularly has a better effect when being used as a hole transmission material of the OLED device.
In addition, researchers find that when the A group is C10-C50 aryl, the A group has better hole transport property and injection property compared with phenyl or heteroaryl, and the performance of the device can be effectively improved.
In the present invention, "substituted group" means a selection range of substituents when a "substituted or unsubstituted" group is substituted, the number is not particularly limited as long as the requirement of a compound bond is satisfied, and exemplarily, 1, 2, 3,4 or 5, and when the number of substituents is 2 or more, the 2 or more substituents may be the same or different.
In the present invention, halogen represents a chlorine atom, a fluorine atom, a bromine atom or the like.
In the present invention, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the invention, aryl comprises monocyclic aryl or fused ring aryl, heteroaryl comprises monocyclic heteroaryl or fused ring heteroaryl, wherein monocyclic aryl means that at least one phenyl is contained in a molecule, and when at least two phenyl are contained in a molecule, the phenyl is independent and connected through a single bond; the fused ring aryl refers to a compound which contains at least two benzene rings in a molecule, but the benzene rings are not independent, but common ring sides are fused with each other; monocyclic heteroaryl means that at least one heteroaryl is contained in a molecule, and when one heteroaryl and other groups (such as aryl, heteroaryl, alkyl and the like) are contained in a molecule, the heteroaryl and the other groups are independent of each other and are connected through a single bond; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings.
The hetero atom in the heteroaryl group in the present invention generally means an atom or group of atoms selected from N, O, S, P, Si and Se, preferably N, O, S. The atomic names given in this disclosure, including their respective isotopes, for example, hydrogen (H) includes 1 H (protium or H), 2 H (deuterium or D), etc.; carbon (C) then comprises 12 C、 13 C and the like.
In the present invention, the number of carbons of the C10-C50 aryl group includes, but is not limited to, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, C48, etc., and the number of carbons of the C6-C30 aryl group includes, but is not limited to, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, etc., and is exemplarily selected from the following groups: fluorenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, perylene,
Figure BDA0002903741900000021
A phenyl group or a tetracenyl group. In particular, the biphenyl group is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; terphenyl 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 and a 2-naphthyl group; the anthracene group is selected from 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 and fluorenyl derivatives; the fluorenyl derivative is selected from 9, 9-dimethylfluorene, 9-spirobifluorene, 9 diphenylfluorene, spirofluorene and benzofluorene; the pyrenyl is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl.
In the present invention, the C6-C30 arylamino represents a group formed by substituting one or two C6-C30 aryl groups for hydrogen on an amino group, wherein the linking site of the C6-C30 arylamino group can be linked to an aryl group in the arylamino group or can be linked to N in the arylamino group, and exemplary carbon numbers and specific groups of the C6-C30 aryl group in the C6-C30 arylamino group are the same as those described above.
The number of carbons in the C3-C30 heteroaryl group includes, but is not limited to, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, and the like, and exemplary groups are selected from the following: furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole. C3-C30 heteroarylamino groups and C6-C30 arylamino groups and C6-C30 arylamino groups are the same, and exemplary carbon numbers and specific groups of the C3-C30 heteroaryl groups in the C3-C30 heteroarylamino groups are the same as those described above.
The C1-C20 chain alkyl group includes branched alkyl groups and straight chain alkyl groups, preferably C1-C10 chain alkyl groups, the number of carbons includes but is not limited to C1, C2, C3, C4, C5, C6, C7, C8, C9 and the like, and examples thereof include: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl and the like.
C3-C20 cycloalkyl is preferably C3-C10 cycloalkyl, the number of carbons includes, but is not limited to, C4, C5, C6, C7, C8, C9 and the like, and examples thereof include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
C1-C20 alkoxy is preferably C1-C10 alkoxy, the number of carbons includes but is not limited to C1, C2, C3, C4, C5, C6, C7, C8, C9 and the like, and exemplary groups of alkyl in alkoxy are the same as described above; the number of carbons in the C1-C6 thioalkoxy group includes, but is not limited to, C2, C3, C4, C5, and the like.
C1-C20 thioalkoxy is preferably C1-C6 thioalkoxy, and the number of carbons includes, but is not limited to, C1, C2, C3, C4, C5, and the like.
Preferably, a is selected from a substituted or unsubstituted C10-C30 aryl group, preferably any one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, further preferably any one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group;
ar is 1 、Ar 2 、Ar 3 And Ar 4 Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C30 arylamino, C6-C30 aryl, C3-C30 heteroaryl and C3-C30 heteroarylamino.
Preferably, the fluorenyl group is selected from the group consisting of a 9,9 dimethylfluorenyl group, a 9,9 diphenylfluorenyl group, or a spirofluorenyl group, preferably a 9,9 dimethylfluorenyl group.
Preferably, Ar is 1 、Ar 2 、Ar 3 And Ar 4 Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothienyl, or carbazolyl.
Preferably, Ar is 1 And Ar 3 Are the same group, said Ar 2 And Ar 4 Are the same group.
Preferably, said A, Ar 1 、Ar 2 、Ar 3 And Ar 4 Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of C1-C20 chain alkyl, C3-C20 cycloalkyl and C1-C20 alkoxy.
Preferably, said A, Ar 1 、Ar 2 、Ar 3 And Ar 4 Wherein each of the substituted groups is independently selected from any one or a combination of at least two of methyl, tert-butyl, cyclohexyl, adamantyl or methoxy.
Preferably, the
Figure BDA0002903741900000031
Each independently selected from any one of the following substituted or unsubstituted groups:
Figure BDA0002903741900000041
the above-mentioned
Figure BDA0002903741900000042
When the substituent groups exist, the substituent groups are respectively and independently selected from any one or at least two combinations of amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C30 arylamino, C6-C30 aryl, C3-C30 heteroaryl and C3-C30 heteroarylamino,
wherein the wavy line indicates the bond of the group.
Furthermore, the invention preferably uses the aromatic amine groups in combination, which is more favorable for improving the performance of the device.
Preferably, the compound has any one of the following structures shown as P1 to P135:
Figure BDA0002903741900000051
Figure BDA0002903741900000061
Figure BDA0002903741900000071
Figure BDA0002903741900000081
Figure BDA0002903741900000091
Figure BDA0002903741900000101
Figure BDA0002903741900000111
Figure BDA0002903741900000121
Figure BDA0002903741900000131
Figure BDA0002903741900000141
Figure BDA0002903741900000151
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 a hole transport material of 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 comprising at least one compound according to one of the objects.
Preferably, the organic layer comprises a hole transport layer containing at least one compound described for one of the purposes.
In one embodiment, the organic layer may include a hole transport region, a light emitting layer, an electron transport region.
In particular embodiments, 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, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used 2 ) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. 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), ytterbium (Yb), 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 also be 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); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
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), or aromatic amine derivatives (such as compounds shown below as HT-1 to HT-51); or any combination thereof.
Figure BDA0002903741900000161
Figure BDA0002903741900000171
Figure BDA0002903741900000181
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-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-HI-3 described below.
Figure BDA0002903741900000191
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 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 BDA0002903741900000192
Figure BDA0002903741900000201
Figure BDA0002903741900000211
Figure BDA0002903741900000221
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 BDA0002903741900000222
Figure BDA0002903741900000231
Figure BDA0002903741900000241
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 BDA0002903741900000242
Figure BDA0002903741900000251
In one aspect of the invention, the light emitting layer employs a 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 BDA0002903741900000252
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more compounds of HT-1 to HT-30, as described above, or one or more compounds of PH-47 to PH-77, as described above; mixtures of one or more compounds from HT-1 to HT-30 and one or more compounds from PH-47 to PH-77 may also be used, but are not limited thereto.
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-73 listed below.
Figure BDA0002903741900000261
Figure BDA0002903741900000271
Figure BDA0002903741900000281
Figure BDA0002903741900000291
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds from ET-1 to ET-73 or one or more compounds from PH-1 to PH-85; mixtures of one or more compounds from ET-1 to ET-73 with one or more compounds from PH-1 to PH-85 may also be used, but are not limited thereto.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ,LiF,NaCl,CsF,Li 2 O,Cs 2 CO 3 ,BaO,Na,Li,Ca，Mg、Yb。
Compared with the prior art, the invention has the following beneficial effects:
the compound provided by the invention forms the optimal steric hindrance effect and a plane structure by matching two arylamine groups substituted at specific positions on a benzene ring with C10-C50 aryl, so that the compound can be used as a hole transport material to be applied to an organic electroluminescent device, and can obtain higher device efficiency, lower driving voltage and longer service life.
Detailed Description
The technical solution of the present invention is further described below by way of specific embodiments. 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.
The synthesis of the compounds of formula I according to the invention is represented by the following scheme:
Figure BDA0002903741900000292
a, Ar as described above 1 、Ar 2 、Ar 3 And Ar 4 All have the same meaning as in formula I, wherein
Figure BDA0002903741900000293
When the two groups are different, the synthesis is carried out by adopting the route II.
The synthesis method of the compound of the present invention belongs to the prior art, and a person skilled in the art can select specific reagents and synthesis conditions according to actual situations. For compounds which are not shown in the following examples in specific synthetic methods, the compounds can be prepared by similar methods, and can be obtained only by replacing raw materials, which are not described in detail herein, or can be prepared by other methods in the prior art by those skilled in the art.
Synthesis example 1:
synthesis of Compound P1
Figure BDA0002903741900000301
Adding 2, 4-dichlorobromobenzene (0.1mol), 2-naphthalene boric acid (0.1mol), potassium carbonate (0.12mol), tetrakis (triphenylphosphine) palladium (0.001mol), water (30mL) and 200mL of dioxane into a reaction bottle, heating to 80 ℃ for reacting for 6h, monitoring the reaction by TLC (thin layer chromatography), adding water and dichloromethane for extraction, separating an organic phase, concentrating, and purifying by column chromatography to obtain M1.
Adding M1(0.05mol), N-phenyl- [1,1' -biphenyl ] -4-amine (0.12mol), sodium tert-butoxide (0.2mol), tris (dibenzylideneacetone) dipalladium (0.0005mol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.001mol, S-Phos) and toluene (200mL) into a reaction bottle, heating to 120 ℃ for reaction for 7h, monitoring the reaction by TLC, cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P1 (mass spectrum test result: 691.3).
Synthesis example 2:
synthesis of Compound P8
The difference from Synthesis example 1 was that N-phenyl- [1,1' -biphenyl ] -4-amine was replaced with N-phenyl-2 (9, 9-dimethyl-9H-fluorene) amine in an equivalent amount to obtain Compound P8 (771.4 as a result of mass spectrometry).
Synthesis example 3:
synthesis of Compound P22
The difference from Synthesis example 1 was that N-phenyl- [1,1' -biphenyl ] -4-amine was replaced with N- (4-tert-butylphenyl) -2(9, 9-dimethyl-9H-fluorene) amine in an equal amount to obtain Compound P22 (mass spectrometry: 883.5).
Synthesis example 4:
synthesis of Compound P29
Figure BDA0002903741900000302
Adding 2, 4-dichlorobromobenzene (0.1mol), 1-naphthalene boric acid (0.1mol), potassium carbonate (0.12mol), tetrakis (triphenylphosphine) palladium (0.001mol), water (30mL) and 200mL of dioxane into a reaction bottle, heating to 80 ℃ for reacting for 6h, monitoring the reaction by TLC (thin layer chromatography), adding water and dichloromethane for extraction, separating an organic phase, concentrating, and purifying by column chromatography to obtain M2.
Adding M2(0.05mol), diphenylamine (0.12mol), sodium tert-butoxide (0.2mol), tris (dibenzylideneacetone) dipalladium (0.0005mol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.001mol, S-Phos) and toluene (200mL) into a reaction bottle, heating to 120 ℃ for reaction for 5 hours, monitoring the reaction by TLC (thin layer chromatography), cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P29 (mass spectrum test result: 539.2).
Synthesis example 5:
synthesis of Compound P56
Figure BDA0002903741900000311
Adding 2, 4-dichlorobromobenzene (0.1mol), 9-dimethylfluorene-2-boric acid (0.1mol), potassium carbonate (0.12mol), tetrakis (triphenylphosphine) palladium (0.001mol), water (30mL) and 200mL of dioxane into a reaction bottle, heating to 80 ℃ for reaction for 6 hours, monitoring the reaction by TLC, adding water and dichloromethane for extraction, separating an organic phase, concentrating, and purifying by column chromatography to obtain M3.
Adding M3(0.05mol), N-phenyl-2-naphthylamine (0.12mol), sodium tert-butoxide (0.2mol), tris (dibenzylideneacetone) dipalladium (0.0005mol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.001mol, S-Phos) and toluene (200mL) into a reaction bottle, heating to 120 ℃ for reaction for 10h, monitoring the reaction by TLC, cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P56 (mass spectrum test result: 705.3).
Synthesis example 6:
synthesis of Compound P93
The difference from Synthesis example 5 was that 9, 9-dimethylfluorene-2-boronic acid was replaced with an equal amount of 9, 9-dimethylfluorene-3-boronic acid and N-phenyl-2-naphthylamine was replaced with an equal amount of N- (toluene-4-yl) - [1,1' -biphenyl ] -4-amine to obtain compound P93 (mass spectrometry: 785.4).
Synthesis example 7:
synthesis of Compound P101
The difference from Synthesis example 4 was that 1-naphthalenedicarboxylic acid was replaced with an equal amount of 9, 9-spirobifluorene-4-boronic acid to obtain compound P101 (mass spectrometry: 727.3).
Synthesis example 8:
synthesis of Compound P112
The difference from Synthesis example 1 was that 2-naphthylboronic acid was replaced with an equal amount of 4-biphenylboronic acid to give compound P112 (mass spectrometry: 717.3).
Synthesis example 9:
synthesis of Compound P113
Figure BDA0002903741900000312
Adding 2, 4-dichlorobromobenzene (0.1mol), 4-biphenylboronic acid (0.1mol), potassium carbonate (0.12mol), tetrakis (triphenylphosphine) palladium (0.001mol), water (30mL) and 200mL of dioxane into a reaction bottle, heating to 80 ℃ for reaction for 4 hours, monitoring the reaction completion by TLC, adding water and dichloromethane for extraction, separating an organic phase, concentrating, and purifying by column chromatography to obtain M4.
Adding M4(0.05mol), N- (4-tert-butylphenyl) -aniline (0.05mol), sodium tert-butoxide (0.07mol), tris (dibenzylideneacetone) dipalladium (0.00025mol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.0005mol, S-Phos) and toluene (200mL) into a reaction bottle, heating to 90 ℃ for reaction for 5 hours, monitoring the reaction by TLC, cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P113-A.
P113-A (0.03mol), N- (4-tert-butylphenyl) - [1,1' -biphenyl ] -4-amine (0.04mol), sodium tert-butoxide (0.07mol), tris (dibenzylideneacetone) dipalladium (0.0003mol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.0006mol, S-Phos) and xylene (150mL) are added into a reaction bottle, heated to 140 ℃ for reaction for 5 hours, TLC is used for monitoring the reaction completion, water and dichloromethane are added for extraction after cooling, and the organic phase is concentrated and purified by column chromatography to obtain P113 (mass spectrum test result: 753.4).
Synthesis example 10:
synthesis of Compound P119
The difference from Synthesis example 1 was that N-phenyl- [1,1' -biphenyl ] -4-amine was replaced with N- (4-tert-butylphenyl) -dibenzofuran-4-amine in an equal amount to give compound P119 (mass spectrometry: 831.4).
Synthesis example 11:
synthesis of Compound P125
The difference from Synthesis example 5 was that N-phenyl-2-naphthylamine was replaced with an equal amount of N- (dibenzofuran-4-yl) -aniline to obtain Compound P125 (mass spectrometry: 785.3)
Synthesis example 12:
synthesis of Compound P133
Figure BDA0002903741900000321
The difference from Synthesis example 1 was that 2-naphthylboronic acid was replaced with an equivalent of 9-phenanthreneboronic acid, and N-phenyl- [1,1' -biphenyl ] -4-amine was replaced with an equivalent of 4-tert-butyl-N-phenylaniline to give a compound P133 (mass spectrometry: 701.4).
Comparative Synthesis example 1
Synthesis of Compound C3
The difference from Synthesis example 1 was that 2-naphthylboronic acid was replaced with an equivalent amount of phenylboronic acid to give Compound C3 (results of mass spectrometry: 641.3).
Figure BDA0002903741900000322
Example 1
The embodiment provides an organic electroluminescent device, and the specific preparation method is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cationic beam;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10 -5 Pa, performing vacuum thermal evaporation on the anode layer film to form a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer, 60nm compound HT-4 as a first hole transport layer, and 5nm compound P1 as a second hole transport layer in sequence; a binary mixture of a compound PH-34 of 40nm and RPD-10(100:3, w/w) is used as a light-emitting layer; 5nm of ET-23 as a hole blocking layer, 25nm of a mixture of compounds ET-69: ET-57(50/50, w/w) as an electron transport layer, 1nm of LiF as an electron injection layer, and 150nm of metallic aluminum as a cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Examples 2 to 13 and comparative examples 1 to 3 differ from example 1 only in the material of the second hole transport layer, which is described in detail in table 1.
The structure of the second hole transport layer material used in the comparative example was as follows:
Figure BDA0002903741900000331
wherein, C1 is detailed in patent application CN107531684A, C2 is detailed in patent application US20150376114A1,
performance testing
The following performance measurements were performed for the organic electroluminescent devices provided in examples and comparative examples:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples and the lifetime of the devices were measured at the same luminance using a digital source meter and a luminance meter. 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/m 2 The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT97 is as follows: using a luminance meter at 10000cd/m 2 The luminance drop of the organic electroluminescent device was measured to be 9700cd/m with a constant current maintained at luminance 2 Time in hours.
In the performance test results, the measurement data of comparative example 1 is set as reference data (counted as 1), and other data are ratios to comparative example 1, which are detailed in table 1.
TABLE 1
Figure BDA0002903741900000332
Figure BDA0002903741900000341
As can be seen from table 1, the novel organic material provided by the present invention can produce more excellent performance through the collocation of specific substituents. When the material is used for an organic electroluminescent device, the current efficiency can be effectively improved, the driving voltage can be effectively reduced, the service life of the device can be prolonged, and the material is a hole transport material with good performance.
Compared with comparative example 1, the difference of the invention is that the substituent of the group A is different, the invention adopts aryl of C10-C50, C1 adopts heterocyclic structure of dibenzofuran, and the data shows that the hole transport capability is weaker than that of the invention, so that the voltage, the efficiency and the service life are all poorer than that of the invention.
Compared with comparative example 2, the present invention is distinguished by that aryl group (i.e. group a) is substituted at ortho position of only one aromatic amine in the compound, and aryl group substitution is present at ortho position of the bisarylamine in the compound C2, which results in that the spatial structure of the molecule is distorted too much, which is not beneficial to hole transmission, which results in much worse transmission, higher voltage, lower efficiency, and the luminescent recombination center is biased to the second hole transmission layer due to worse transmission, and the lifetime is also reduced.
The second hole transport material used in comparative example 3, in which the aromatic ring is substituted at the ortho position to the aromatic amine, is inferior in transport to the C10-C50 aromatic group of the present invention as seen from the voltage efficiency, resulting in inferior performance to the material of the present invention as a whole.
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 (10)

1. A compound having a structure according to formula I;
Figure FDA0002903741890000011
in the formula I, A is selected from substituted or unsubstituted C10-C50 aryl;
in the formula I, Ar is 1 、Ar 2 、Ar 3 And Ar 4 Each independently selected fromAny one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
in the A, the substituted groups are respectively and independently selected from any one or at least two combinations of amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C30 arylamino and C6-C30 aryl;
ar is 1 、Ar 2 、Ar 3 And Ar 4 Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 thioalkoxy, C6-C30 arylamino, C6-C30 aryl, C3-C30 heteroaryl and C3-C30 heteroarylamino.
2. A compound according to claim 1, wherein a is selected from a substituted or unsubstituted C10-C30 aryl group, preferably any one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, further preferably any one of a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group;
preferably, the fluorenyl group is selected from the group consisting of a 9,9 dimethylfluorenyl group, a 9,9 diphenylfluorenyl group, or a spirofluorenyl group, preferably a 9,9 dimethylfluorenyl group.
3. The compound of claim 1 or 2, wherein Ar is 1 、Ar 2 、Ar 3 And Ar 4 Each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, fluorenyl, dibenzofuranyl, dibenzothienyl, or carbazolyl;
ar is 1 、Ar 2 、Ar 3 And Ar 4 Wherein each of the substituted groups is independently selected from amino, cyano, halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, halogen,Any one or at least two of C1-C20 thioalkoxy, C6-C30 arylamino, C6-C30 aryl, C3-C30 heteroaryl and C3-C30 heteroarylamino.
4. The compound of claim 1 or 2, wherein Ar is 1 And Ar 3 Are the same group, said Ar 2 And Ar 4 Are the same group.
5. A compound according to claim 1 or 2, wherein A, Ar is the compound 1 、Ar 2 、Ar 3 And Ar 4 Wherein, the substituted groups are respectively and independently selected from any one or at least two combinations of C1-C20 chain alkyl, C3-C20 cycloalkyl and C1-C20 alkoxy;
preferably, said A, Ar 1 、Ar 2 、Ar 3 And Ar 4 Wherein each of the substituted groups is independently selected from any one or a combination of at least two of methyl, tert-butyl, cyclohexyl, adamantyl or methoxy.
6. The compound of claim 1, wherein said compound is selected from the group consisting of
Figure FDA0002903741890000021
Each independently selected from any one of the following substituted or unsubstituted groups:
Figure FDA0002903741890000031
when said
Figure FDA0002903741890000032
When a substituent group is present, the substituent group is the same as in claim 1;
wherein the wavy line indicates the bond of the group.
7. The compound of claim 1, wherein the compound has any one of the following structures P1-P135:
Figure FDA0002903741890000041
Figure FDA0002903741890000051
Figure FDA0002903741890000061
Figure FDA0002903741890000071
Figure FDA0002903741890000081
Figure FDA0002903741890000091
Figure FDA0002903741890000101
Figure FDA0002903741890000111
Figure FDA0002903741890000121
Figure FDA0002903741890000131
Figure FDA0002903741890000141
8. use of a compound according to any one of claims 1 to 7 in an organic electroluminescent device.
9. Use according to claim 8, wherein the compound is used as a hole transport material in the organic electroluminescent device.
10. 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 comprising at least one compound according to any one of claims 1 to 7;
preferably, the organic layer comprises a hole transport layer comprising at least one compound according to any one of claims 1 to 7.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113563203A (en) * 2021-07-30 2021-10-29 上海钥熠电子科技有限公司 Compound based on m-phenylenediamine and application thereof in organic electroluminescent display device

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113563203A (en) * 2021-07-30 2021-10-29 上海钥熠电子科技有限公司 Compound based on m-phenylenediamine and application thereof in organic electroluminescent display device
CN113563203B (en) * 2021-07-30 2024-03-01 上海钥熠电子科技有限公司 M-phenylenediamine-based compound and application thereof in organic electroluminescent display device

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