CN113004154B - Compound and application thereof - Google Patents

Compound and application thereof Download PDF

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CN113004154B
CN113004154B CN201911307588.4A CN201911307588A CN113004154B CN 113004154 B CN113004154 B CN 113004154B CN 201911307588 A CN201911307588 A CN 201911307588A CN 113004154 B CN113004154 B CN 113004154B
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CN113004154A (en
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王志鹏
张维宏
黄金华
曾礼昌
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Beijing Eternal Material Technology Co Ltd
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    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
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    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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Abstract

The invention discloses a compound and application thereof, wherein the compound has a structure shown in a formula (I), and is used as a luminescent material in an organic electroluminescent device, the organic electroluminescent device comprises a substrate, a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, and any one or at least two of the compounds are contained in the organic layer; the compound has better chemical stability and electron transmission capability, is used for an organic electroluminescent device, and can effectively reduce the starting voltage and improve the luminous efficiency.

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
Organic light-emitting diodes (OLEDs), which are organic semiconductors as functional materials, are a new generation of all-solid-state flat panel display technologies, and currently, OLED display technologies have been adopted for all-purpose in daily life, such as smartphones, smartwatches, portable notebooks, and the like. Compared with other display technologies, the OLED technology has the advantages of wide viewing angle, high response speed, low driving voltage, wide adaptable display temperature range, realization of full-color display from blue light to red light spectrum region and the like.
The research of the OLED is very intensive at present, and the device structure of the OLED is that organic functional layers are added between an anode and a cathode, and the functional layers comprise hole injection, hole transmission, a light emitting area, electron transmission and electron injection. In order to balance the transport rate of electrons or holes, an electron blocking layer is sometimes added between the hole transport layer and the light emitting layer, or a hole blocking layer is added between the electron transport layer and the light emitting layer. Through certain energy level collocation, holes and electrons can be gathered in the luminous main body layer to collide, so that the luminous material can excite luminescence. However, at present, further improvements on the performance of the OLED display, such as driving voltage, efficiency, display lifetime, etc., are required to achieve a more practical purpose. There is a need for continued efforts to develop organic light emitting devices having low voltage driving, high efficiency, high luminance and long life.
The organic hole material plays an important role in transferring holes injected from the anode to the light emitting layer, and the hole transport material having excellent hole mobility is advantageous for injection balance of carriers in the device, thereby realizing reduction of device driving voltage. On the other hand, excitons generated in the light-emitting layer move to the hole-transporting layer, and eventually emit light at the interface between the hole-transporting layer and the light-emitting layer, resulting in problems of color shift and reduction in light-emitting efficiency. Therefore, in order to improve the efficiency of the light emitting layer, an electron blocking layer needs to be added between the hole transport layer and the light emitting layer to prevent efficiency roll-off and improve the stability of the device.
Therefore, it is highly necessary to develop a compound which is excellent in performance and can be used in an organic electroluminescent device.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a compound having the structure of formula (I):
In the formula (I), R 1 is selected from any one of isopropyl, tert-butyl, isobutyl, cyclopentyl, cyclohexyl or cycloheptyl;
In the formula (I), ar 1 is selected from any one of substituted or unsubstituted C10-C30 (such as C10, C12, C14, C16, C18, C20, C26, C28, C30 and the like) aryl, substituted or unsubstituted C10-C30 (such as C10, C12, C14, C16, C18, C20, C26, C28, C30 and the like) heteroaryl;
In the formula (I), ar 2 is selected from any one of substituted or unsubstituted C6-C30 (such as C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30 and the like) aryl, substituted or unsubstituted C3-C30 (such as C3, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30 and the like) heteroaryl;
In formula (I), each of L 1 and L 2 is independently selected from any of a single bond, a substituted or unsubstituted C1 to C20 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) alkylene, a substituted or unsubstituted C6 to C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) arylene, a substituted or unsubstituted C3 to C30 (e.g., C3, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroarylene;
In the formula (I) of the present invention, the R 2、R3 and R 4 are each independently selected from the group consisting of substituted or unsubstituted C1-C20 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) catenated alkyl, substituted or unsubstituted C3-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, etc.) C18, C19, C20, etc.), a substituted or unsubstituted C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10) chain alkoxy, a substituted or unsubstituted C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, C10) cycloalkoxy, a substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10) alkenyl, a substituted or unsubstituted C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10) alkynyl, halogen, cyano, nitro, acyl, ester, hydroxy, silane, amino, substituted or unsubstituted C6-C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) arylamino, substituted or unsubstituted C3-C30 (e.g., C3, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroarylamino, substituted or unsubstituted C6-C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) aryl, substituted or unsubstituted C3-C30 (e.g., C3, C4, C8, C10, C12, C18, C12, C18, C28, C18, C16, C18, etc.) heteroaryl amino C30, etc.) heteroaryl;
In the formula (I), m is an integer of 0 to 5 (for example, 0, 1, 2,3, 4, 5), n is an integer of 0 to 4 (for example, 0, 1, 2,3, 4), and p is an integer of 0 to 3 (for example, 0, 1, 2, 3); if the value of m is greater than 1, at least two R 4 are substituted on the parent ring, at least two R 4 can be selected from the same group or different groups, and the parent ring can be selected and adjusted according to actual needs by a person skilled in the art; the same applies to n and p; if m, n or p are greater than 1, the corresponding selection criteria of R 4、R2、R3 are the same as those of the above, and will not be described in detail;
When a substituent is present on the above-mentioned group, the substituents are selected from halogen, C1-C20 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.), chain alkyl, C3-C20 (e.g., C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.), cycloalkyl, C1-C6 (e.g., C1, C2, C3, C4, C5, C6) alkoxy, C1-C6 (e.g., C1, C2, C3, C4, C5, C6) thioalkoxy, C6-C30 (e.g., C6, C8, C10) any one or a combination of at least two of C12, C14, C16, C18, C20, C26, C28, C30, etc.) arylamino, C3 to C30 (e.g., C3, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) heteroarylamino, C6 to C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) monocyclic aryl or fused ring aryl, C3 to C30 (e.g., C3, C4, C5, C6, C8, C10, C12, C14, C16, C18, C20, C26, C28, C30, etc.) monocyclic heteroaryl fused ring heteroaryl; the range of substituents for the "substituted group" in the above-mentioned "substituted or unsubstituted group" is the range of substituents herein; when the number of the substituents is 1, any one of the substituents can be selected from the range, and when the number of the substituents is multiple, the same substituent can be selected, or different substituents can be selected, so that the person skilled in the art can select according to actual needs; if a "substituted or unsubstituted group" appears hereinafter, the selection range and selection criteria of the substituted substituent are the same as those described herein, and the description thereof will be omitted.
In the present invention, the heteroatoms in the "heteroaryl" groups referred to are generally selected from any one or a combination of at least two of N, O or S; hereinafter, if reference is made to "heteroaryl", the selection of the heteroatoms is the same as that described herein, and detailed description thereof will be omitted.
In the present invention, the expression of the ring structure of the "-" indicates that the linking site is at any position on the ring structure that can be bonded; in the following, the meaning of expression is the same as that of the ring structure marked by "-" and detailed description is omitted.
The compound provided by the invention takes aniline as a parent ring, and the substituted or unsubstituted C10-C30 aryl and the substituted or unsubstituted C10-C30 heteroaryl are introduced in the ortho position of the aniline, so that the charge transmission is enhanced, the charge mobility of molecules is improved, the voltage of a device is reduced, the efficiency roll-off of the device is inhibited, and the service life of the device is prolonged; in addition, isopropyl, tertiary butyl, isobutyl, cyclopentyl, cyclohexyl or cycloheptyl are introduced into the compound, and are different from long-chain alkyl, the long-chain alkyl can generate free rotation motion along the carbon axis direction, so that the tight stacking among molecules is not facilitated, and the charge transmission is affected; secondly, the chemical structure of saturated alkane is relatively stable, and the influence on the spatial arrangement of molecules is small, so that the higher transmission efficiency is facilitated; the chemical property of the re-saturated alkane is stable, so that the stability of the molecule under special environments, such as oxidation in air, can be improved; the chemical stability and charge transport properties of the compounds can be improved by the use of the parent ring in combination with specific types of substituents.
The compound provided by the invention is applied to an organic electroluminescent device, can effectively reduce the starting voltage of the organic electroluminescent device and improves the current efficiency.
Preferably, the compound has a structure represented by formula (II);
In formula (II), R 1、R2、R3、R4、Ar1、Ar2、L1、L2, m, n, and p all have the same defined ranges as before.
In the invention, the structure shown in the formula (II) is preferable, and arylene is substituted at the para position of the parent ring aromatic amine, so that the steric hindrance can be reduced, the stability of the compound structure can be conveniently increased, the starting voltage of the organic electroluminescent device can be further reduced, and the current efficiency of the device can be improved.
Preferably, the compound has the structure of formula (III):
In formula (III), R 1、R2、R3、R4、Ar1、Ar2、L1、L2, m, n and p all have the same defined range as in claim 1.
In the invention, the structure shown in the formula (III) is preferable, R 1 is substituted at the para position of L 1, so that the steric hindrance can be reduced, the stability of the structure of the compound can be conveniently increased, the starting voltage of the organic electroluminescent device can be further reduced, and the current efficiency of the device can be improved.
Preferably, the R 1 is selected from any one of cyclopentyl, cyclohexyl, or cycloheptyl;
Preferably, R 1 is cyclohexyl.
Preferably, ar 1 is selected from any one of substituted or unsubstituted C10-C30 condensed ring aryl, substituted or unsubstituted C10-C30 condensed ring heteroaryl;
Preferably, ar 1 is selected from any one of substituted or unsubstituted 9, 9-dimethylfluorene, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene;
Preferably, ar 1 is selected from any one of 9, 9-dimethylfluorene, biphenyl, dibenzofuran or dibenzothiophene;
Preferably, ar 1 is 9, 9-dimethylfluorene.
In the invention, ar 1 is preferably selected from the groups, has higher electron mobility and high thermal stability, and is convenient for reducing the starting voltage and current efficiency of the organic electronic device.
Preferably, the compound has the structure of formula (IV):
In formula (IV), R 2、R3、R4、Ar2、L1、L2, m, n, and p all have the same defined ranges as before;
preferably, the compound has the structure of formula (V):
In formula (V), R 2、R3、R4、Ar2、L1、L2, m, n, and p all have the same defined ranges as before.
In the invention, the compound has a specific structure of formula (V), and the fluorenyl group with 2-position substitution can improve the conjugation capability of molecules, thereby being beneficial to the improvement of carriers.
Preferably, each of L 1 and L 2 is independently selected from any one of a single bond, a substituted or unsubstituted C6-C30 arylene group;
Preferably, each of said L 1 and L 2 is independently selected from a single bond or a C6-C30 arylene group;
preferably, each of L 1 and L 2 is independently selected from a single bond or phenylene.
Preferably, m is 0, n is 0, and p is 0.
In the present invention, the purpose of m, n, p are preferably 0 is: because of the introduction of excessive functional group substitution, the unstable factors in the molecular electrochemical environment are increased, the service life of the device is influenced, and the compound with larger molecular weight is not easy to evaporate, so that the compound with simple structure is designed as far as possible on the premise of not influencing the charge transmission performance and the luminous efficiency of the compound.
Preferably, ar 2 is selected from any one of the following groups:
Wherein the dashed line represents the access site of the group.
Preferably, the compound has any one of the following C1-C344 structures:
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It is a second object of the present invention to provide the use of a compound according to one of the objects, said compound being useful in an organic electroluminescent device.
Preferably, the compound is used as a hole transport material or an electron blocking material of an organic electroluminescent device.
It is a third object of the present invention to provide an organic electroluminescent device including a substrate, a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode; the organic layer comprises any one or a combination of at least two of the compounds described previously.
Preferably, the organic layer comprises a hole transport layer comprising any one or a combination of at least two of the compounds according to one of the objects.
Preferably, the organic layer comprises an electron blocking layer comprising any one or a combination of at least two of the compounds according to one of the objects.
The organic electroluminescent device provided by the invention comprises a first electrode, a second electrode and an organic material layer positioned between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
In one aspect of the present invention, the material of the hole transport region may be selected from one or more compounds of formula I of the present invention, the electron blocking layer of the hole transport region may be absent, or may be, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 through HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-12 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
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In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
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Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of YPD-1 through YPD-11 listed below.
In one aspect of the invention, the light-emitting layer employs a technique of thermally activating delayed fluorescence emission. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of TDE-1 through TDE-39 listed below.
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In one aspect of the invention, the light-emitting layer employs a technique of thermally activating delayed fluorescence emission. The host material of the light emitting layer is selected from, but not limited to, one or more of TDH1 to TDH 24.
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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, combinations of one or more of ET-1 through ET-57 listed below.
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The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following: liQ, liF, naCl, csF, li 2O、Cs2CO3, baO, na, li or Ca.
Compared with the prior art, the invention has the following beneficial effects:
The compound provided by the invention takes aniline as a parent ring, and the substituted or unsubstituted C10-C30 aryl and the substituted or unsubstituted C10-C30 heteroaryl are introduced in the ortho position of the aniline, so that the charge transmission is enhanced, the charge mobility of molecules is improved, and the voltage of a device is reduced; the efficiency roll-off of the device can be restrained, and the service life of the device is prolonged; in addition, isopropyl, tertiary butyl, isobutyl, cyclopentyl, cyclohexyl or cycloheptyl are introduced into the compound, and are different from long-chain alkyl, the long-chain alkyl can generate free rotation motion along the carbon axis direction, so that the tight stacking among molecules is not facilitated, and the charge transmission is affected; secondly, the chemical structure of saturated alkane is relatively stable, and the influence on the spatial arrangement of molecules is small, so that the higher transmission efficiency is facilitated; the chemical property of the re-saturated alkane is stable, so that the stability of the molecule under special environments, such as oxidation in air, can be improved; the chemical stability and charge transport properties of the compounds can be improved by the use of the parent ring in combination with specific types of substituents. The compound is applied to an organic electroluminescent device, can effectively reduce the starting voltage of the organic electroluminescent device and improve the current efficiency.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
The synthetic route of the compounds of formula (I) according to the invention:
in specific embodiments, the preparation and synthesis can be performed according to the above-described route; wherein X is any one of chlorine, bromine, iodine or triflate groups, but is not limited to the groups listed above; r 1、R2、R3、R4、L1、L2、Ar1 and Ar 2 each have the same selection ranges as above.
The synthesis method of the compound provided by the present invention belongs to a conventional method, and a person skilled in the art can synthesize the compound by the prior art, and by way of example, several typical synthesis methods of the compound in the following preparation examples are provided.
All compounds of the synthesis process not mentioned in the present invention are commercially available starting products. The solvents and reagents used in the present invention, such as N-bromosuccinimide, petroleum ether, ethyl acetate, potassium carbonate, N-dimethylacetamide, anhydrous sodium sulfate, 4-bromodiphenyl, sodium t-butoxide, palladium tetraphenyl phosphine, ammonium chloride, and other chemical reagents, can be purchased from domestic chemical product markets, such as from the national pharmaceutical group reagent company, TCI company, shanghai Bi, pharmaceutical company, carboline reagent company, and the like. In addition, the person skilled in the art can synthesize the compounds by known methods.
Analytical detection of intermediates and compounds in the present invention used ABSCIEX mass spectrometer (4000 QTRAP).
The intermediate M of the compound of formula (I) can be prepared by the following method:
(1) Synthesis of intermediate-1:
The preparation method comprises the following steps: 4-aminobiphenyl (15.0 g,62 mmol) was dissolved in 300mL of a solvent of N, N-dimethylformamide, placed in a three-necked flask equipped with a constant pressure dropping funnel, and cooled to 0℃with an ice-water bath. N-bromosuccinimide (11 g,62 mmol) was dissolved in 150mL of N, N-dimethylformamide, placed in a constant pressure dropping funnel, and the solution was slowly dropped in a reaction flask, keeping the temperature of the reaction between 0℃and 5℃for about one hour, after the completion of the dropping, the reaction was further kept for half an hour, the reaction was monitored for complete reaction, and then the reaction solution was poured into 1000mL of ice water, extracted with ethyl acetate (500 mL, three times), the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated to give a brown oil, and purified by a silica gel column (petroleum ether/ethyl acetate, 10/1) to give a yellow solid (20 g).
Structural characterization: MS (M+H): 248.
(2) Synthesis of intermediate M:
the preparation method comprises the following steps: intermediate-1 (10.0 g,33 mmol), 2-boric acid-9, 9-dimethylfluorene (8.2 g,35 mol), potassium carbonate (6.2 g,40.1 mmol) were placed in a 1000mL three-necked flask, stirred well, then the air on the flask was replaced with nitrogen three times, and tetrakis triphenylphosphine palladium (350 mg,0.303 mmol) was added to the reaction solution under nitrogen protection, then the temperature was raised to 100℃and reacted for 18 hours. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (500 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a reddish brown oil. The crude product was purified by silica gel chromatography (petroleum ether/ethyl acetate, 10/1) to give 20g of a pale yellow solid.
Structural characterization: MS (M+H): 362.
Synthesis example 1
Synthesis of compound C1:
(1) Preparation of Compound C1-1
Intermediate M (10 g,27.7 mmol), 4-bromobiphenyl (6.6 g,28.3 mmol) and sodium tert-butoxide (2.8 g,29.4 mmol) were taken and placed in a 250mL three-necked flask containing 130mL toluene, and dissolved with sufficient stirring. The air in the flask was then fully purged with nitrogen, followed by adding the catalyst tris (dibenzylideneacetone) dipalladium (207 mg,0.226 mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (200 mg,0.452 mmol) to the reaction solution and heating to reflux for 18h. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (200 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a brown-black oil. The crude product was purified by column chromatography on silica gel (petroleum ether/dichloromethane, 5/1) to give 12g of a white solid.
Structural characterization: MS (M+H): 514.
(2) Preparation of Compound C1
Intermediate C1-1 (10 g,19.4 mmol), 4-cyclohexylbromobenzene (5.6 g,23.3 mmol) and sodium tert-butoxide (2.1 g,21.8 mmol) were taken and placed in a 250mL three-necked flask containing 130mL toluene, and dissolved with sufficient stirring. The air in the flask was then fully purged with nitrogen, and then tris (dibenzylideneacetone) dipalladium (154 mg,0.168 mmol) and 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (138 mg,0.336 mmol) as catalysts were added to the reaction solution and the mixture was warmed to reflux for 18h. After cooling, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with ethyl acetate (200 mL, three times), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to a brown-black oil. The crude product was purified by column chromatography on silica gel (petroleum ether/dichloromethane, 8/1) to give 10g of a white solid. The product was recrystallized twice from toluene and ethanol to give 5g of the product with a purity of 99.8%.
Structural characterization: MS (M+H): 672.
Synthesis examples 2 to 16 were conducted in the same manner as in Synthesis example 1 except that the raw materials were replaced, as shown in Table 1:
TABLE 1
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Example 1
The embodiment provides an organic electroluminescent device, which is prepared by the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
Placing the glass substrate with the anode in a vacuum cavity, vacuumizing to less than 1X 10 -5 Pa, and vacuum evaporating HT-4:HI-3 (97/3,w/w) on the anode layer film as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
vacuum evaporation C1 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 60nm;
vacuum evaporation HT-14 is continued on the hole transport layer to serve as an electron blocking layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 35nm;
Vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate is 0.1nm/s by utilizing a multi-source co-evaporation method, the total evaporation film thickness is 40nm, and a ternary mixture of a compound GPH-46:GPH-3:GPD-12 (100:100:20, w/w/w) is used as the luminescent layer;
Vacuum evaporating electron transport layer material ET-46:ET-57 (50/50, w/w) of the device on the light emitting layer, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 25nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
So that it has the following structure:
ITO/HT-4:HI-3(97/3,w/w,10nm)/C1(60nm)/HT-14(35nm)/GPH-46:GPH-3:GPD-12(100:100:20,w/w/w)(30nm)/ET-46:ET57(50/50,w/w)(25nm)/LiF(0.5nm)/Al(150nm).
Examples 2 to 7, comparative examples 1 to 3 and example 1 differ only in that the hole transport layer materials were replaced with the compounds listed in table 2.
The structure of the compound in the comparative example is as follows:
performance tests were performed on examples 1-7 and comparative examples 1-3:
The driving voltage and current efficiency of the organic electroluminescent devices prepared in examples and comparative examples were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was raised at a rate of 0.1V per second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent device reached 10000cd/m 2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency.
The results of the performance test are shown in Table 2:
TABLE 2
As can be seen from Table 2, the OLED devices in the examples had a starting voltage as low as 4.7-4.9V and a current efficiency as high as 51.4-54.9 cd/A; the device has better luminous efficiency and lower driving voltage.
The hole transport material of the device of example 3 was C46, which differs from R-1 of comparative example 1 in that adamantane in R-1 was replaced with cyclohexyl, and a 2-substituted 9, 9-dimethylfluorene was added in the ortho position of the amine-based benzene ring. Example 3 has significantly improved device performance over comparative example 1.
Similarly, in example 3, compared with comparative example 2, the hole transporting material used in comparative example 2 was R-2, and C46 was different from R-2 in that the n-butyl group in R-2 was substituted with cyclohexyl group and a 2-substituted 9, 9-dimethylfluorene was added in the ortho position of the amine-based benzene ring. The device performance of example 3 is better than that of comparative example 2.
The hole transport material of the device of comparative example 3 was R-3, and the device of comparative example 3 was inferior in voltage and efficiency to example 6, as compared to example 6.
The results prove that when the compound provided by the invention is used as a hole transport material of an OLED device, the luminous efficiency of the device can be effectively improved, and the starting voltage is reduced, because the compound provided by the invention takes aniline as a parent ring, substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C10-C30 heteroaryl are introduced at the ortho position of parent amine, and isopropyl, tert-butyl, isobutyl, cyclopentyl, cyclohexyl or cycloheptyl is introduced at a specific position in the compound, the compound has better chemical stability and charge transport performance, and the hole transport material of the compound used for the OLED device can improve the luminous efficiency of the device and reduce the driving voltage of the device.
Example 8
The embodiment provides an organic electroluminescent device, which is prepared by the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
Placing the glass substrate with the anode in a vacuum cavity, vacuumizing to less than 1X 10 -5 Pa, and vacuum evaporating HT-4:HI-3 (97/3,w/w) on the anode layer film as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
Vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 60nm;
Vacuum evaporation C4 is continued on the hole transport layer to serve as an electron blocking layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 35nm;
vacuum evaporating a luminescent layer of the device on the hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate is 0.1nm/s by utilizing a multi-source co-evaporation method, the total evaporation film thickness is 40nm, and a ternary mixture of a compound GPH-46:GPH-3:GPD-12 (100:100:20, w/w/w) is used as the luminescent layer;
Vacuum evaporating electron transport layer material (ET-46, 50% ratio setting and ET-57, 50% ratio setting) of the device on the light emitting layer, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 25nm;
LiF with the thickness of 0.5nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 150nm serves as a cathode of the device.
So that it has the following structure:
ITO/HT-4:HI-3(97/3,w/w)(10nm)/HT-4(60nm)/C4(35nm)/GPH-46:GPH-3:GPD-12(100/100/2,w/w/w,40nm)/ET46:ET57(50/50,w/w,25nm)LiF(0.5nm)/Al(150nm).
Examples 9 to 14, comparative examples 4 to 6 and example 8 differ only in that the materials of the electron transport layer were replaced with the compounds listed in table 3; the performance test method is the same as that of example 1.
TABLE 3 Table 3
As can be seen from Table 3, the OLED devices in the examples had a starting voltage as low as 3.8-4.0V and a current efficiency as high as 63.3-65.8 cd/A; the device has better luminous efficiency and lower driving voltage. The compound provided by the invention is also an electron blocking layer material with good performance.
The electron blocking material in example 8 was C4 and the electron blocking material of the device of comparative example 4 was R-1. C4 differs from R-1 in that the alkyl group in C4 is cyclohexyl, R-1 is adamantane, and C4 introduces 2-substituted 9, 9-dimethylfluorene in the ortho position of the amino benzene ring. The device data of example 8 are all superior to comparative example 4.
Likewise, example 8 is compared to the device of comparative example 5. The electron blocking material in the device of comparative example 5 was replaced with R-2. C4 differs from R-2 in that the alkyl group in C4 is cyclohexyl, R-2 is n-butyl, and C4 introduces 2-substituted 9, 9-dimethylfluorene in the ortho position of the amino benzene ring. Example 8 has improved device data performance over comparative example 5.
The electron blocking material used in example 13 was C244 and that of the device of comparative example 6 was R-3. C244 is different from R-3 in that the alkyl group used for C244 is cyclohexyl, the alkyl group for R-3 is t-butyl, and C244 is 9, 9-dimethylfluorene substituted at the 2-position ortho position to the amine-based benzene ring. Example 13 has improved performance over the device data ratio of comparative example 6.
The results prove that when the compound provided by the invention is used as an electron blocking material of an OLED device, the luminous efficiency of the device can be effectively improved, and the starting voltage is reduced, because the compound provided by the invention takes aniline as a parent ring, substituted or unsubstituted C10-C30 aryl and substituted or unsubstituted C10-C30 heteroaryl are introduced at the ortho position of parent amine, and isopropyl, tert-butyl, isobutyl, cyclopentyl, cyclohexyl or cycloheptyl is introduced at a specific position in the compound, the compound has better chemical stability and charge transmission performance, and the electron blocking material of the compound used for the OLED device can improve the luminous efficiency of the device, and reduce the driving voltage of the device.
The applicant declares that the above is only a specific embodiment of the present invention, but the scope of the present invention is not limited thereto, and it should be apparent to those skilled in the art that any changes or substitutions that are easily conceivable within the technical scope of the present invention disclosed by the present invention fall within the scope of the present invention and the disclosure.

Claims (16)

1. A compound, characterized in that the compound has the structure of formula (I):
In formula (I), R 1 is cyclohexyl;
in the formula (I), ar 1 is selected from any one of substituted or unsubstituted 9, 9-dimethylfluorene, substituted or unsubstituted dibenzofuran and substituted or unsubstituted dibenzothiophene;
In the formula (I), ar 2 is selected from any one of substituted or unsubstituted C6-C20 aryl and substituted or unsubstituted C3-C20 heteroaryl;
In the formula (I), L 1 and L 2 are independently selected from any one of single bond and arylene of C6-C20;
In the formula (I), R 2、R3 and R 4 are independently selected from any one of C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 chain alkoxy and C6-C20 aryl;
in the formula (I), m is an integer of 0-2, n is an integer of 0-2, and p is 0 or 1;
When the above-mentioned groups have substituents, the substituents are selected from any one of C1-C10 chain alkyl groups, C3-C10 cycloalkyl groups, C1-C6 alkoxy groups, C1-C6 thioalkoxy groups, C6-C20 monocyclic aryl groups or condensed ring aryl groups.
2. The compound of claim 1, wherein the compound has a structure represented by formula (II):
In formula (II), R 1、R2、R3、R4、Ar1、Ar2、L1、L2, m, n and p all have the same defined range as in claim 1.
3. The compound of claim 2, wherein the compound has the structure of formula (III):
In formula (III), R 1、R2、R3、R4、Ar1、Ar2、L1、L2, m, n and p all have the same defined range as in claim 1.
4. A compound according to any one of claims 1 to 3, wherein Ar 1 is selected from any one of 9, 9-dimethylfluorene, dibenzofuran or dibenzothiophene.
5. A compound according to any one of claims 1 to 3 wherein Ar 1 is 9, 9-dimethylfluorene.
6. A compound according to claim 3, wherein the compound has the structure of formula (IV):
in formula (IV), R 2、R3、R4、Ar2、L1、L2, m, n and p all have the same defined range as claim 3.
7. A compound according to claim 3, wherein the compound has the structure of formula (V):
in formula (V), R 2、R3、R4、Ar2、L1、L2, m, n and p all have the same defined range as claim 3.
8. The compound of any one of claims 1-3, 6-7, wherein each of L 1 and L 2 is independently selected from a single bond or a phenylene group.
9. A compound according to any one of claims 1-3, 6-7, wherein m is 0, n is 0, and p is 0.
10. A compound according to any one of claims 1 to 3, 6 to 7, wherein Ar 2 is selected from any one of the following groups:
Wherein the dashed line represents the access site of the group.
11. The compound of claim 1, wherein the compound has any one of the following C1-C344 structures:
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12. use of a compound according to any one of claims 1-11, characterized in that the compound is applied in an organic electroluminescent device.
13. The use according to claim 12, characterized in that the compound is used as hole transport material or electron blocking material for organic electroluminescent devices.
14. An organic electroluminescent device, characterized in that the organic electroluminescent device comprises a substrate, a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode; the organic layer comprises any one or a combination of at least two of the compounds of any one of claims 1-11.
15. The organic electroluminescent device of claim 14, wherein the organic layer comprises a hole transport layer comprising any one or a combination of at least two of the compounds of any one of claims 1-11.
16. The organic electroluminescent device of claim 14, wherein the organic layer comprises an electron blocking layer comprising any one or a combination of at least two of the compounds of any one of claims 1-11.
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