CN113429393B - Anthracene-indole derivative, material for organic electroluminescent element, light-emitting element, and consumer product - Google Patents

Anthracene-indole derivative, material for organic electroluminescent element, light-emitting element, and consumer product Download PDF

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CN113429393B
CN113429393B CN202110985402.1A CN202110985402A CN113429393B CN 113429393 B CN113429393 B CN 113429393B CN 202110985402 A CN202110985402 A CN 202110985402A CN 113429393 B CN113429393 B CN 113429393B
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organic electroluminescent
anthraindole
compound
derivative
electroluminescent element
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CN113429393A (en
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韩洪波
赵雷
唐伟
谢佩
李程辉
刘殿君
唐怡杰
边坤
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Beijing Bayi Space LCD Technology Co Ltd
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Abstract

The invention provides an anthraindole derivative, a material for an organic electroluminescent element, a light-emitting element, and a consumer product. The structure of the anthraindole derivative is shown in a formula (I). The anthraindole derivatives of the present invention can be used as a host material for a fluorescent or phosphorescent emitter, or used as a host material together with other host materials and phosphorescent emitters, and can significantly improve the luminous efficiency and lifetime of a light-emitting element, and lead to a steep current-voltage curve in use and at low operating voltages. The anthraindole derivative has high thermal stability, and can be decomposed and residue-freeThe compound of the present invention has high oxidation stability and good long-term storage stability when subjected to sublimation.
Figure 282093DEST_PATH_IMAGE001
Formula (I).

Description

Anthracene-indole derivative, material for organic electroluminescent element, light-emitting element, and consumer product
Technical Field
The invention relates to the technical field of luminescent materials, in particular to an anthraindole derivative, a material for an organic electroluminescent element, a luminescent element and a consumer product.
Background
As early as 1963, pope et al first discovered the electroluminescence phenomenon of organic compound single crystal anthracene, and started organic electroluminescence (abbreviated as OLED) and related research. Through development of twenty years, the organic light-emitting (abbreviated as EL) material has comprehensively realized red, blue and green light emission, and the application field is also expanded from small molecules to the fields of high molecules, metal complexes and the like.
In recent years, organic electroluminescent display technology has become mature, some products have entered the market, but in the process of industrialization, many problems still need to be solved. In particular, many problems have not been solved in the carrier injection and transport properties, the electroluminescent properties of the materials, the service life, the color purity, the matching between various materials and between various electrodes, and the like of various organic materials used for manufacturing elements. Especially, the light emitting element has not yet achieved practical requirements in terms of luminous efficiency and service life, which greatly limits the development of OLED technology. The metal complex phosphorescent material utilizing triplet state luminescence has high luminescence efficiency, green and red materials of the metal complex have already met the use requirements, but the metal complex has special electronic structure characteristics, so that the blue material of the metal complex cannot meet the use requirements.
Under the current technological development, improvements are also needed, both for fluorescent materials and for phosphorescent materials, in particular in terms of operating voltage, efficiency and lifetime for use in organic electroluminescent devices and thermal stability during sublimation.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides an anthraindole derivative for use in a phosphorescent OLED, wherein the anthraindole derivative can be used as a hole transport material in a hole transport layer or an exciton blocking layer or as a host material in a light emitting layer.
In order to achieve the purpose, the invention adopts the following technical scheme:
an anthraindole derivative, wherein the structure of the anthraindole derivative is shown as formula (I):
Figure 215354DEST_PATH_IMAGE001
formula (I)
Wherein R is1~R10Selected, identically or differently on each occurrence, from the group consisting of hydrogen, deuterium, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, preferably an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an arylamino or heteroaromatic ring system having from 5 to 60 carbon atoms, wherein two or more adjacent substituents may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system;
Ar1、Ar2each of which is the same or different and is selected from the group consisting of aromatic or heteroaromatic ring systems having from 5 to 80 carbon atomsPreferably, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an arylamine group or a heteroarylamine group having from 5 to 60 carbon atoms.
Further, said R5~R10Each independently selected from hydrogen or deuterium; r1~R4Each independently selected from the group consisting of hydrogen, deuterium, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, preferably, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an arylamino or heteroaromatic ring system having from 5 to 60 carbon atoms, wherein two or more adjacent substituents may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system.
According to one embodiment of the invention, said R1、R5~R10Is hydrogen; r2~R4Each independently selected from the group consisting of hydrogen, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, preferably, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an arylamine or heteroaromatic group having from 5 to 60 carbon atoms, wherein two or more adjacent substituents may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system.
According to one embodiment of the invention, said R1、R4~R10Is hydrogen; r2、R3Each independently selected from the group consisting of hydrogen, an aromatic or heteroaromatic ring system having from 5 to 80 carbon atoms, preferably, an aromatic or heteroaromatic ring system having from 5 to 60 carbon atoms, an arylamine or heteroaromatic group having from 5 to 60 carbon atoms, wherein two or more adjacent substituents may optionally be joined or fused to form a mono-or polycyclic aliphatic, aromatic or heteroaromatic ring system.
According to one embodiment of the invention, said R1~R10Is hydrogen; ar (Ar)1、Ar2Each identical or different, from the group consisting of aromatic or heteroaromatic ring systems having from 5 to 80 carbon atoms, preferably, aromatic or heteroaromatic ring systems having from 5 to 60 carbon atoms, arylamines or heteroarylamines having from 5 to 60 carbon atoms.
Aryl in the sense of the present invention contains 6 to 60 carbon atoms and heteroaryl in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl herein is considered to mean a simple aromatic ring, i.e. benzene, naphthalene, etc., or a simple heteroaromatic ring, such as pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, such as biphenyl, which are connected to one another by single bonds, are, in contrast, not referred to as aryl or heteroaryl groups, but rather as aromatic ring systems.
Aromatic or heteroaromatic ring systems in the sense of the present invention contain 5 to 60 carbon atoms, wherein the aromatic ring system is built up from benzene, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran and dibenzothiophene or a combination of these groups. An aromatic ring system in the sense of the present invention is also intended to be taken to mean, in particular, a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be linked by a nonaromatic unit, for example C, N, O or an S atom. Thus, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, and the like are also considered to refer to aromatic ring systems in the sense of the present invention.
Alkyl in the sense of the present invention contains 1 to 40 carbon atoms and wherein the individual hydrogen atoms or-CH2The aliphatic hydrocarbon radicals or alkyl or alkenyl or alkynyl radicals which may also be substituted by the abovementioned radicals are preferably to be understood as meaning the following radicals: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, cyclopentyl, n-hexyl, neohexyl, cyclohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl. The alkoxy group, preferably an alkoxy group having 1 to 40 carbon atoms, is considered to mean a methoxy group, a trifluoromethoxy groupEthoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentoxy, sec-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexoxy, n-heptoxy, cycloheptoxy, n-octoxy, cyclooctoxy, 2-ethylhexoxy, pentafluoroethoxy and 2,2, 2-trifluoroethoxy. The heteroalkyl group is preferably an alkyl group having 1 to 40 carbon atoms, meaning a hydrogen atom or-CH alone2The radicals-which may be substituted by oxygen, sulfur or halogen atoms-are understood to mean alkoxy, alkylthio, fluorinated alkoxy, fluorinated alkylthio, in particular methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, trifluoromethylthio, trifluoromethoxy, pentafluoroethoxy, pentafluoroethylthio, 2,2, 2-trifluoroethoxy, 2,2, 2-trifluoroethylthio, vinyloxy, propenyloxy, propenylthio, butenylthio, butenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexenyloxy, cyclohexenylthio, ethynyloxy, propenylthio, butenyloxy, cyclohexenylthio, ethynyloxy, Ethynylthio, propynyloxy, propynylthio, butynyloxy, butynylthio, pentynyloxy, pentynylthio, hexynyloxy, hexynylthio.
In general, the cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, where one or more-CH may be present2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The aromatic or heteroaromatic ring system which may also be substituted in each case by the abovementioned alkyl radicals according to the invention is, in particular, a radical derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, idobenzene, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridecyl, spirotriindene, spiroisotridecyl, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6] quinoline, benzo [6,7] quinoline, benzo [7,8] quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, and the like, Quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazahnthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine and benzothiadiazole or groups derived from combinations of these systems.
Further, the anthraindole derivative comprises one of formulas CJHM077 to CJHM223, and the specific structures of CJHM077 to CJHM223 are as follows:
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a material for an organic electroluminescent element, comprising the anthraindole derivative.
An organic electroluminescent element comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, at least one of the organic layers comprising the anthraindole derivative.
According to one embodiment of the invention, the anthraindole derivative is used as a hole transport layer, a hole injection layer or an exciton blocking layer material in an organic electroluminescent element.
According to one embodiment of the present invention, the anthraindole derivative is used as a host material for a fluorescent emitter or a phosphorescent emitter in an organic electroluminescent device.
According to one embodiment of the present invention, the organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of light emitting layers. I.e. a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the compounds according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole-injecting and hole-transporting layer and in the electron-injecting and electron-transporting layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10-5The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, compounds of formula (I) of the present invention are modified by appropriate substitution to obtain soluble compounds. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
In a further embodiment of the present invention, the organic electroluminescent element according to the invention does not comprise a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, i.e. the light-emitting layer is directly adjacent to the hole injection layer or the anode and/or the light-emitting layer is directly adjacent to the electron transport layer or the electron injection layer or the cathode.
These methods are generally known to those skilled in the art, and they can be applied to an organic electroluminescent element comprising the compound according to the present invention without inventive labor.
The invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, at least one layer being applicable by means of a sublimation method and/or by means of an organic vapour deposition method or by means of carrier gas sublimation and/or by spin coating or by means of a printing method from solution.
Furthermore, the present invention relates to a composition comprising at least one of the compounds indicated above. The same preferences as indicated above for the organic electroluminescent elements apply to the compounds according to the invention. In particular, the compounds may furthermore preferably comprise further compounds. The processing of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires the preparation of the compounds according to the invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferred to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchylone, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, methyl benzoate, p-xylene, methyl benzoate, mesitylene, and mixtures thereof, Cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol butyl methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, 2-isopropylnaphthalene, pentylbenzene, hexylbenzene, heptylbenzene, octylbenzene, 1-bis (3, 4-dimethylphenyl) ethane, or a mixture of these solvents.
These methods are generally known to those skilled in the art and can be applied by him, without inventive effort, to organic electroluminescent elements comprising the compounds according to the invention.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A consumer product comprising an organic electroluminescent element comprising a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, the organic layer material comprising the anthraindole derivative.
The consumer product of the present invention comprises one of the following products: a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior lighting and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cellular telephone, a tablet computer, a phablet, a Personal Digital Assistant (PDA), a wearable device, a laptop computer, a digital camera, a video camera, a viewfinder, a microdisplay at a diagonal of less than 2 inches, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video wall containing multiple displays tiled together, a theater or stadium screen, a phototherapy device, and a sign.
Compared with the prior art, the invention has the beneficial effects that:
(1) the anthraindole derivatives of the present invention are very suitable for use in a hole transporting or electron blocking layer in an organic electroluminescent element, and also in a layer directly adjacent to a phosphorescent light-emitting layer, since the compounds of the present invention do not annihilate light emission;
(2) the anthraindole derivatives of the present invention can be used as a host material for a fluorescent or phosphorescent emitter, or used as a host material together with other host materials and phosphorescent emitters, and can significantly improve the luminous efficiency and lifetime of a light-emitting element, and lead to a steep current-voltage curve in use and at low operating voltages.
(3) The anthraindole derivative of the present invention has high thermal stability, can be sublimed without decomposition and residue, and has high oxidation stability and good long-term storage stability.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a schematic view of a bottom emission example of an organic electroluminescent element of the present invention;
fig. 2 is a schematic diagram of an example of top emission of an organic electroluminescent element of the present invention.
Reference numerals
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport/electron blocking layer, 5-luminescent layer, 6-hole transport/electron transport layer, 7-electron injection layer and 8-cathode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The preparation method of the invention is a conventional method unless otherwise specified. The starting materials used are available from published commercial sources unless otherwise specified, and the percentages are by mass unless otherwise specified.
The following examples are provided for testing the performance of OLED materials and devices using the following test apparatus and method:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Example 1
The preparation of compound D-1, comprising the steps of:
the first step is as follows: preparation of Compound A-1
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36.9 mmol of 2, 7-dibromo-9-phenylcarbazole (CAS:444796-09-2) was dissolved in 150.0 mL of glacial acetic acid, 14.5 mmol of potassium iodate, 24.0 mmol of potassium iodide, and a drop of concentrated sulfuric acid were added, the mixture was heated under reflux and stirred for reaction for 2 hours, cooled to room temperature, filtered, the filter cake was washed with water and a saturated aqueous solution of sodium bisulfite, and was separated and purified by a silica gel column to obtain Compound A-1 as a white solid with a yield of 87%.
The second step is that: preparation of Compound B-1
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20.0 mmol of compound A-1 is dissolved in 120 mL of dry THF, the temperature is reduced to 0 ℃ under the protection of nitrogen, 24.0 mmol of 1M isopropyl magnesium bromide THF solution is added dropwise, the mixture is stirred and reacted for 1 hour, then 24.0 mmol of phthalic anhydride solution in THF is added dropwise, the mixture is stirred and reacted for 1 hour, the temperature is raised to room temperature, 50 mL of 2N diluted hydrochloric acid aqueous solution is added, the mixture is extracted by ethyl acetate, the organic phase is collected and dried, the filtrate is concentrated under reduced pressure and dried, and the filtrate is recrystallized by acetone, thus obtaining compound B-1, white solid with the yield of 90%.
The third step: preparation of Compound C-1
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196.5 mmol zinc powder and 4.0 mmol mercury chloride are mixed, 30 mL water and 1 mL concentrated hydrochloric acid are added, the mixture is stirred and reacted for 2 hours at room temperature, the water in the reaction solution is poured out and is washed by water twice, 15.0 mL water, 3.5 mL concentrated hydrochloric acid, 18.0 mL toluene and 18.0 mL 1, 4-dioxane are added, 29.75 mmol intermediate B-1 is added, the temperature is raised to reflux and stirring and reaction for 48 hours, 9.0 mL concentrated hydrochloric acid is slowly added in a dropwise manner during the reaction, the temperature is reduced to room temperature, 100 mL water is added, the mixture is extracted by ethyl acetate, an organic phase is collected, dried and concentrated under reduced pressure to obtain a white solid with the yield of 75 percent.
The fourth step: preparation of Compound D-1
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10.0 mmol of C-1 is dissolved in 200 mL of dry dichloromethane, 2.0 mmol of trifluoroacetic acid is added under the protection of nitrogen, the mixture is stirred and reacted for 2 hours at room temperature, 50 mL of water is added, the dichloromethane is used for extraction, the organic phase is collected, dried and concentrated under reduced pressure, the residue is stirred and dissolved by 40 mL of THF and 80 mL of ethanol, 53.0 mmol of sodium borohydride is added, the mixture is stirred and reacted for 30 minutes, 120 mL of water is added, concentrated hydrochloric acid is added to adjust the acidity, the dichloromethane is used for extraction, the organic phase is collected, dried and concentrated under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain yellow solid D-1, and the yield is 87%.
Referring to the synthesis of compound D-1, the following compounds were prepared:
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example 2
A process for the preparation of compound G-1 comprising the steps of:
the first step is as follows: preparation of Compound E-1
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Dissolving 50.0 mmol of D-2 in 110 mL of dry dichloromethane, cooling to 0 ℃, dropwise adding 55.0 mmol of boron tribromide solution in dichloromethane, stirring for reaction for 2 hours, pouring the reaction solution into 200 mL of saturated sodium bicarbonate aqueous solution, extracting with dichloromethane, collecting an organic phase, drying, filtering, concentrating and drying the filtrate under reduced pressure, and separating and purifying by using a silica gel column to obtain a compound E-1, namely a white solid, wherein the yield is 96%.
The second step is that: preparation of Compound F-1
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45.0 mmol of E-1 is dissolved in 100 mL of dry dichloromethane, 80.0 mmol of pyridine is added, the temperature is reduced to 0 ℃ under the protection of nitrogen, 54.0 mmol of trifluoromethanesulfonic anhydride solution in dichloromethane is added dropwise, the mixture is stirred and reacted for 1 hour, the mixture is heated to room temperature and stirred and reacted for 2 hours, 50 mL of 2N dilute hydrochloric acid aqueous solution is added, dichloromethane is used for extraction, an organic phase is collected, dried, concentrated and dried under reduced pressure, and separated and purified by a silica gel column, so that the compound F-1 is obtained, white solid and the yield is 87%.
The third step: preparation of Compound G-1
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40.0 mmol of F-1 are dissolved in 80 mL of DMF, 48.0 mmol of pinacol diboride, 60.0 mmol of anhydrous potassium acetate, 0.4 mmol of Pd (dppf) Cl are added under nitrogen protection2And 0.4 mmol of iodoidene, heating to 90 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 100 mL of saturated aqueous sodium bicarbonate solution, extracting with ethyl acetate, collecting an organic phase, drying, concentrating under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the compound G-1, a yellow solid with the yield of 82%.
Referring to the synthesis of compound G-1, the following compounds were prepared:
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example 3
Preparation of compound CJHM 089:
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12.0 mmol of G-1, 10.0 mmol of 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (CAS:864377-31-1), 36.0 mmol of anhydrous sodium carbonate, and 0.01 mmol of Pd (PPh)3)4Catalyst, 40 mL of toluene,20 mL of ethanol and 20 mL of water are heated under reflux and stirred to react for 12 hours under the protection of nitrogen, the mixture is cooled to room temperature, 60 mL of water is added to dilute the mixture, the mixture is filtered, a filter cake is washed by water and ethanol, the filter cake is dried and then is separated and purified by a silica gel column, and the compound CJHM089 is obtained as a white solid with the yield of 87%. MS (MALDI-TOF): m/z =651.2564 [ M + H [ ]]+；1HNMR（δ、CDCl3）：9.02~9.00(2H, d), 8.81~8.78(5H, m), 8.48~8.40(4H, m), 8.16~8.14(1H, d), 8.04~8.01(1H, m), 7.63~7.60(1H, m), 7.57~7.47(10H, m), 7.45~7.39(3H, m), 7.36~7.28(3H, m)。
Referring to the synthesis of compound CJHM089, the following compound was prepared:
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example 4
Preparation of compound CJHM 121:
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22.0 mmol of bis ([1,1' -Biphenyl)]-4-yl) amine (CAS:102113-98-4), 20.0 mmol of compound F-1, 30.0 mmol of sodium tert-butoxide, and further 0.1 mmol of Pd2(dba)3CHCl3The catalyst, 0.15 mL of 30% tri-tert-butylphosphine toluene solution and 80 mL of toluene are heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 12 hours, cooled to room temperature, diluted by adding 50 mL of water, extracted by dichloromethane, the organic phase is dried, filtered, the filtrate is concentrated and dried under reduced pressure, and separated and purified by a silica gel column to obtain the compound CJHM121 as a white solid with the yield of 79%. MS (MALDI-TOF): m/z =663.2818 [ M + H [ ]]+；1HNMR(δ、CDCl3): 8.87(1H, s), 8.69(1H, s), 8.46~8.44(1H, d), 8.40~8.37(1H, m), 7.95~7.93(1H, d), 7.65~7.61(1H, m), 7.58~7.54(6H, m), 7.51~7.43(8H, m), 7.39~7.30(5H, m), 7.28~7.22(5H, m), 7.18~7.14(4H, m)。
Referring to the synthesis of compound CJHM121, the following compounds were prepared:
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example 5
Preparation of compound CJHM 154:
the first step is as follows: preparation of Compound H-1
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20.0 mmol of D-3, 22.0 mmol of pinacol diboron and 30.0 mmol of anhydrous potassium acetate are added, 0.05 mmol of palladium acetate, 0.2 mmol of cuprous iodide, 0.1 mmol of Xphos and 60 mL of DMF are added, the mixture is heated to 90 ℃ under the protection of nitrogen and stirred for reaction for 12 hours, the mixture is cooled to room temperature, 120 mL of water is added for dilution, the mixture is extracted by ethyl acetate, organic phase is dried, filtered, filtrate is concentrated and dried under reduced pressure, and is separated and purified by a silica gel column, so that the compound H-1 is obtained, white solid and the yield is 90%.
The second step is that: preparation of Compound I-1
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Compound I-1 was prepared in 85% yield as a white solid by substituting G-1 in example 3 with H-1 and 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine with 2-chloro-4, 6-diphenyl-1, 3, 5-triazine with the synthetic procedure in example 3.
The third step: preparation of Compound J-1
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Referring to the synthesis methods of the first and second steps in example 2, compound J-1 was prepared in 78% yield by replacing only D-2 of the first step in example 2 with I-1.
The fourth step: preparation of compound CJHM154
Figure 675436DEST_PATH_IMAGE052
13.0 mmol of phenylboronic acid, 10.0 mmol of J-1, 36.0 mmol of anhydrous potassium carbonate, and 0.01 mmol of Pd (PPh)3)4The catalyst, 40 mL of toluene, 20 mL of ethanol and 20 mL of water are heated under reflux and stirred to react for 12 hours under the protection of nitrogen, the reaction product is cooled to room temperature, 50 mL of water is added to dilute the reaction product, the reaction product is filtered, a filter cake is washed by water and ethanol, the filter cake is dried and then is separated and purified by a silica gel column, and the compound CJHM154 is obtained as a white solid with the yield of 92%. MS (MALDI-TOF): m/z =651.2566 [ M + H [ ]]+；1HNMR(δ、CDCl3)：9.05(1H, s), 8.96(1H, s), 8.81~8.78(5H, m), 8.58~8.55(2H, m), 8.44~8.41(2H, m), 8.37(1H, s), 8.27~8.25(1H, d), 7.98~7.96(1H, d), 7.68~7.64(1H, m), 7.59~7.35(14H, m), 7.32~7.28(1H, m)。
Referring to the synthesis of compound CJHM154, the following compound was prepared:
Figure 368586DEST_PATH_IMAGE053
Figure 882612DEST_PATH_IMAGE054
Figure 370226DEST_PATH_IMAGE055
Figure 193870DEST_PATH_IMAGE056
Figure 362814DEST_PATH_IMAGE057
Figure 996927DEST_PATH_IMAGE058
example 6
Preparation of compound CJHM 182:
the first step is as follows: preparation of Compound K-1
Figure 389862DEST_PATH_IMAGE059
20.0 mmol ofN-phenyl- [1,1' -biphenyl]-4-amine (CAS:32228-99-2), 22.0 mmol of Compound D-3, 30.0 mmol of sodium tert-butoxide, and a further 0.1 mmol of Pd2(dba)3CHCl3The catalyst, 0.15 mL of 30% tri-tert-butylphosphine toluene solution and 80 mL of toluene are heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 12 hours, cooled to room temperature, diluted by adding 50 mL of water, extracted by dichloromethane, dried by an organic phase, filtered, concentrated and dried by reduced pressure, and separated and purified by a silica gel column to obtain the compound K-1, a white solid, and the yield is 89%.
The second step is that: preparation of Compound L-1
Figure 555264DEST_PATH_IMAGE060
Referring to the synthesis methods of the first and second steps in example 2, compound L-1 was prepared in a white solid with a yield of 75% by replacing only D-2 of the first step in example 2 with K-1.
The third step: preparation of compound CJHM182
Figure 75369DEST_PATH_IMAGE061
Referring to the synthesis of the fourth step in example 5, compound CJHM182 was prepared in a white solid with a yield of 87% by replacing only J-1 of the fourth step in example 5 with L-1. MS (MALDI-TOF): m/z =663.2818 [ M + H [ ]]+；1HNMR(δ、CDCl3)：8.95(1H, s), 8.79(1H, s), 8.58~8.55(2H, m), 8.43~8.41(1H, d), 8.37(1H, s), 8.37(1H, s), 8.01~7.98(1H, d), 7.75~7.73(1H, d), 7.68~7.54(6H, m), 7.51~7.45(5H, m), 7.39~7.21(5H, m), 7.03~6.97(5H, m), 6.93~6.89(2H, m), 6.54~6.51(2H, m)。
Referring to the synthesis of compound CJHM182, the following compound was prepared:
Figure 49142DEST_PATH_IMAGE062
Figure 65508DEST_PATH_IMAGE063
as shown in fig. 1 and 2, the OLED element provided by the present invention includes a substrate 1, an anode 2, a cathode 8, and layers 3 to 7 disposed between the anode 2 and the cathode 8. A hole-blocking/electron-transporting layer 6 and an electron-injecting layer 7 are disposed between the cathode 8 and the light-emitting layer 5, and a hole-injecting layer 3 and a hole-transporting/electron-blocking layer 4 are disposed between the light-emitting layer 5 and the anode 2.
An organic electroluminescent element was prepared as follows using a compound represented by the following formula C as a hole injection layer material, a compound represented by the following formula D as a hole transport layer material, a compound represented by the following formula H as an electron blocking layer material, and a compound represented by the following formula a as a green host material of a light-emitting layer, a compound represented by the following formula B as a green dopant material of a light-emitting layer, a compound represented by the following formula G as a dopant material of an electron transport layer, and LiQ as a host material of an electron transport layer.
Figure 124731DEST_PATH_IMAGE064
Figure 448527DEST_PATH_IMAGE065
A compound C (350 a)/D (350 a)/H (1200 a)/a + B (3%) (300 a)/LiQ + G (50%) (350 a)/LiF (10 a)/Al (2 nm) was sequentially evaporated onto an ITO glass using an EL evaporator manufactured by DOV corporation to fabricate a light-emitting element, and an organic electroluminescent element was prepared as comparative example 1.
Organic electroluminescent element prepared by using anthraindole derivative
In comparative example 1 of the organic electroluminescent element, an organic electroluminescent element was fabricated in the same manner except that the compound a was replaced with the compounds CJHM077 to CJHM223 of the present invention: ITO/C (350A)/D (350A)/H (1200)/[ compound of the invention ] + B (3%) (300A)/LiQ + G (50%) (350A)/LiF (10A)/Al (2 nm).
The performance of the resulting element is the result of the test at 1000 nits for the element brightness and the data for voltage, current efficiency (LE) and decay lifetime LT90% are normalized to the comparative example 1 element and the results are shown in table 1.
Table 1: results of device performance test
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Figure 605019DEST_PATH_IMAGE067
Figure 666385DEST_PATH_IMAGE068
Figure 511981DEST_PATH_IMAGE069
Figure 414340DEST_PATH_IMAGE070
Figure 585559DEST_PATH_IMAGE071
Figure 947270DEST_PATH_IMAGE072
Figure 845824DEST_PATH_IMAGE073
Figure 179854DEST_PATH_IMAGE074
Figure 210389DEST_PATH_IMAGE075
Figure 465921DEST_PATH_IMAGE076
Figure 433746DEST_PATH_IMAGE077
As is clear from Table 1, the organic material of the present invention has a low driving voltage of the device, a high luminous efficiency, a good color purity, and a long life of the device using the compound of the present invention as a host material for a light-emitting layer under the condition that the initial emission luminance of the device is 1000 nits.
In comparative example 1 of the organic electroluminescent element, an organic electroluminescent element was fabricated in the same manner except that the compound H was replaced with the compounds CJHM077 to CJHM223 of the present invention: ITO/C (350A)/D (350A)/[ inventive compound ] (1200A)/A + B (3%) (300A)/LiQ + G (50%) (350A)/LiF (10A)/Al (2 nm).
The performance of the resulting element is the result of the test at 1000 nits for the element brightness and the data for voltage, current efficiency (LE) and decay lifetime LT90% are normalized to the comparative example 2 element and the results are shown in table 2.
TABLE 2 test results of device Properties
Figure 356703DEST_PATH_IMAGE078
Figure 932040DEST_PATH_IMAGE079
Figure 691180DEST_PATH_IMAGE080
Figure 682270DEST_PATH_IMAGE081
Figure 912263DEST_PATH_IMAGE082
Figure 596185DEST_PATH_IMAGE083
Figure 842621DEST_PATH_IMAGE084
Figure 699718DEST_PATH_IMAGE085
Figure 862847DEST_PATH_IMAGE086
Figure 904621DEST_PATH_IMAGE087
Figure 622041DEST_PATH_IMAGE088
Figure 971245DEST_PATH_IMAGE089
As is clear from the results of the element performance test in table 2, the element prepared from the organic material of the present invention has significantly reduced driving voltage, improved luminous efficiency, and better color purity of emitted light, and under the condition that the initial luminance of the element emitted light is 1000 nits, the lifetime of the element LT90% using the compound of the present invention as a hole transport layer material is much better.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.

Claims (6)

1. An anthraindole derivative, wherein the anthraindole derivative comprises one of the formulas CJHM077 to CJHM223, and the specific structures of CJHM077 to CJHM223 are as follows:
Figure 591279DEST_PATH_IMAGE001
Figure 988762DEST_PATH_IMAGE002
Figure 780001DEST_PATH_IMAGE003
Figure 921132DEST_PATH_IMAGE004
Figure 481427DEST_PATH_IMAGE005
Figure 315390DEST_PATH_IMAGE006
Figure 328346DEST_PATH_IMAGE007
Figure 7589DEST_PATH_IMAGE008
Figure 422390DEST_PATH_IMAGE009
Figure 427255DEST_PATH_IMAGE010
Figure 927506DEST_PATH_IMAGE011
Figure 416300DEST_PATH_IMAGE012
Figure 951186DEST_PATH_IMAGE013
Figure 126953DEST_PATH_IMAGE014
Figure 114500DEST_PATH_IMAGE015
Figure 401125DEST_PATH_IMAGE016
。
2. a material for an organic electroluminescent element, comprising the anthraindole derivative according to claim 1.
3. An organic electroluminescent element comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises the anthraindole derivative according to claim 1.
4. The organic electroluminescent element according to claim 3, wherein the anthraindole derivative is used as a material for a hole transport layer, a hole injection layer or an exciton blocking layer in the organic electroluminescent element.
5. The organic electroluminescent element according to claim 4, wherein the anthraindole derivative is used as a host material for a fluorescent emitter or a phosphorescent emitter in the organic electroluminescent element.
6. A consumer product comprising an organic electroluminescent element comprising a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer material comprises the anthraindole derivative of claim 1.
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