CN114907179B - Anthracene derivative, and organic electroluminescent material, light-emitting device and consumer product using same - Google Patents

Anthracene derivative, and organic electroluminescent material, light-emitting device and consumer product using same Download PDF

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CN114907179B
CN114907179B CN202210659236.0A CN202210659236A CN114907179B CN 114907179 B CN114907179 B CN 114907179B CN 202210659236 A CN202210659236 A CN 202210659236A CN 114907179 B CN114907179 B CN 114907179B
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organic electroluminescent
layer
anthracene derivative
light
organic
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CN114907179A (en
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曹建华
姜卫东
张九敏
姜坤
李程辉
刘殿君
唐伟
唐怡杰
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Shanghai 800 Million Spacetime Advanced Material Co ltd
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Abstract

The invention relates to an anthracene derivative, an organic electroluminescent material, a light-emitting device and a consumer product, wherein the anthracene derivative has a novel organic electroluminescent compound with a large steric hindrance non-planar structure formed by anthracene and fluorene, and fluorene and spirobifluorene derivatives increase molecular steric hindrance, prevent the generation of an organic intermolecular excitation-excitation compound, improve internal quantum efficiency, and have a shorter light-emitting wavelength compared with the existing compound, so that the efficiency and service life of an organic electroluminescent device containing the compound are improved; in addition, the compound improves the solubility of the solution and solves the problems of productivity and cost of the process of the prior blue light material.

Description

Anthracene derivative, and organic electroluminescent material, light-emitting device and consumer product using same
Technical Field
The invention belongs to the technical field of organic electroluminescence, and particularly relates to an anthracene derivative, an organic electroluminescent material using the anthracene derivative, a light-emitting device and a consumer product.
Background
Most of the materials used in the organic electroluminescent element are pure organic materials or organometallic complexes of organic materials and metals, and they are classified into hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and the like, depending on the application. Here, an organic substance having a relatively small ionization energy is mainly used as the hole injection substance or the hole transport substance, and an organic substance having a relatively large electronegativity is mainly used as the electron injection substance or the electron transport substance. Further, the substance used as the light-emitting auxiliary layer preferably satisfies the following characteristics:
First, the materials used in the organic electroluminescent element are required to have good thermal stability because joule heat is generated by charge transfer in the organic electroluminescent element, and at present, the glass transition temperature of the materials generally used as the hole transport layer is low, so that the phenomenon of lowering of light emission efficiency due to crystallization occurs at the time of driving at low temperature occurs. Second, in order to reduce the driving voltage, it is necessary to design the organic matter adjacent to the cathode and anode to have a small charge injection barrier and high charge mobility. Third, there is always an energy barrier at the interface of the electrode and the organic layer, and at the interface of the organic layer and the organic layer, and some charges are inevitably accumulated, so that it is necessary to use a substance excellent in electrochemical stability.
The light-emitting layer is composed of two substances, i.e., a host light-emitting body and a dopant, and the dopant needs to have high quantum efficiency, and the host light-emitting body needs to have a larger energy gap than the dopant, so that energy transfer to the dopant is likely to occur. Displays for televisions, mobile devices, etc. realize full colors according to three primary colors of red, green, blue, and the light emitting layer is composed of a red main light emitter/dopant, a green main light emitter/dopant, and a blue main light emitter/dopant, respectively. At present, the blue light material still has the problems of low luminous quantum efficiency and poor color purity. The main reason for this situation is that blue light comes from the transition between energy levels with wider energy gaps, while organic compounds with wide forbidden bands have certain difficulties in molecular design, and secondly, blue light materials have stronger pi-pi bond interaction and have strong charge transfer characteristics in the system, so that more non-radiative relaxation channels exist in the wide energy gaps, fluorescence quenching among molecules is aggravated, and quantum yield of the blue light system is reduced.
The present invention has been made in view of the above-mentioned circumstances.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides an anthracene derivative, an organic electroluminescent material, a light emitting device and a consumer product using the anthracene derivative, wherein the anthracene derivative emits light in blue to deep blue and has high light emitting efficiency.
The first object of the present invention is to provide an anthracene derivative.
The second object of the present invention is to provide an organic electroluminescent material.
A third object of the present invention is to provide an organic electroluminescent device.
A fourth object of the present invention is to provide a consumer product.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
An anthracene derivative, wherein the structural general formula of the anthracene derivative is shown as a formula (I) or a formula (II):
wherein X 1 to X 8 each independently represent N or CR 3;
R 1、R2、R3 is, at each occurrence, identical or different and is selected from the group consisting of hydrogen, deuterium, straight-chain alkyl having C 1-C40, straight-chain heteroalkyl having C 1-C40, branched or cyclic alkyl having C 3-C40, branched or cyclic heteroalkyl having C 3-C40, alkenyl or alkynyl having C 2-C40, an aromatic or aromatic ring system having 5 to 80, preferably 6 to 60, carbon atoms or a heteroaromatic or heteroaromatic ring system having 2 to 60 carbon atoms, or two or more adjacent groups may optionally be cyclic or fused to each other to form a ring;
Ar 1、Ar2、Ar3、Ar4 is each independently selected from the group consisting of hydrogen, deuterium, an aromatic or aromatic ring system having 6 to 60 carbon atoms, or a heteroaromatic or heteroaromatic ring system having 2 to 60 carbon atoms; ar 3 and Ar 4 may be linked to each other by a single bond, O, S, N, or a bridging group of C to form a ring; or Ar 1 and Ar 3 or Ar 4 in formula (II) are linked to each other by a single bond, O, S, N, or a bridging group of C to form a ring.
Aryl groups in the sense of the present invention contain 6 to 60 carbon atoms; heteroaryl groups in the sense of the present invention contain 2 to 60 carbon atoms and at least one heteroatom, provided that the sum of carbon atoms and heteroatoms is at least 5, said heteroatoms preferably being selected from N, O or S. Aryl or heteroaryl is herein 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, such as anthracene, phenanthrene, quinoline, isoquinoline, etc. Aromatic rings, for example biphenyls, which are linked to one another by single bonds are conversely not referred to as aryl or heteroaryl groups, but as aromatic ring systems or heteroaromatic ring systems.
An aromatic or heteroaromatic ring system in the sense of the present invention is intended to be understood as meaning 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 non-aromatic units, for example C, N, O or S atoms. Thus, for example, as well as systems in which two or more aryl groups are linked by, for example, a short alkyl group, systems such as fluorene, 9' -spirobifluorene, 9-diaryl fluorene, triarylamine, diaryl ether, etc., are also considered to refer to aromatic or heteroaromatic ring systems in the sense of the present invention.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl and the like. Heteroalkyl means that the hydrogen atom on the alkyl group or-CH 2 -is substituted with at least one heteroatom selected from halogen, cyano, N, O, S or silicon, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, cyano, ethylcyano, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like.
The alkenyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, and the like.
Alkynyl as used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
In general, cycloalkyl, cycloalkenyl according to the present invention refers to monovalent functional groups derived from the removal of one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. As non-limiting examples thereof, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, wherein one or more-CH 2 -groups may be replaced by the above groups; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or cyano groups.
The heterocycloalkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having a atomic number of 3 to 40. At this time, one or more carbons, preferably 1 to 3 carbons, in the ring are substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine, and the like are given.
The alkoxy group used in the present invention means a monovalent functional group represented by RO -, and the above-mentioned R is an alkyl group having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure. Non-limiting examples of such alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, cyclopentoxy, cyclohexyloxy, and the like.
The aryloxy group used in the present invention means a monovalent functional group represented by R 'O -, and R' is an aryl group having 6 to 60 carbon atoms. As non-limiting examples of such aryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, and the like.
According to the invention, aromatic or heteroaromatic ring systems, the atoms of which may also be substituted in each case by the abovementioned radicals R 1, are in particular radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzine, terphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, trimeric indene, heterotrimeric indene, spirotrimeric indene, spiroheterotrimeric indene, 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, naphthazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxalinoimidazole, oxazole, benzoxazole, naphthooxazole, anthracenoxazole, phenanthrooxazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazabenzophenanthrene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diazaanthracene, 2, 7-diazapyrene, 2, 3-diazapyrene, 1, 6-diazapyrene, 1, 8-diazapyrene, 4, 5-diazapyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorored, naphthyridine, azacarbazole, benzocarboline, 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, and, 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, each of the X 1～X8 is N or CH; r 1、R2 is hydrogen; ar 1、Ar2 is each independently selected from the group consisting of hydrogen, deuterium, an aromatic or aromatic ring system having 6 to 60 carbon atoms, or a heteroaromatic or heteroaromatic ring system having 2 to 60 carbon atoms; ar 3、Ar4 is each independently selected from the group consisting of aromatic or aromatic ring systems having 6 to 60 carbon atoms.
Further, the heteroaromatic or heteroaromatic ring system is a group consisting of groups represented by II-1 to II-17 and aromatic rings or aromatic ring systems, and the specific structures of II-1 to II-17 are as follows:
Wherein each Z 1、Z2 is independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazino, hydrazone, carboxyl or carboxylate thereof, sulfonate or sulfonate thereof, phosphate or phosphate thereof, C 1-C40 alkyl, C 2-C40 alkenyl, C 2-C40 alkynyl, C 1-C40 alkoxy, C 3-C40 naphthene, C 3-C40 cycloalkenyl, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 6-C60 aryloxy, substituted or unsubstituted C 6-C60 arylthio, or substituted or unsubstituted C 2-C60 heteroaryl;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
t 1 represents an oxygen atom or a sulfur atom;
represents the bond between the substituent and the main structure.
The substituents described in the present invention are selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazino, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1-C40 alkyl, C 2-C40 alkenyl, C 2-C40 alkynyl, C 1-C40 alkoxy, C 3-C40 naphthene, C 3-C40 cycloalkenyl, C 6-C60 aryl, C 6-C60 aryloxy, C 6-C60 arylthio, or C 2-C60 heteroaryl.
As used herein, "combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can contemplate from the applicable list. For example, the alkyl and deuterium atoms can combine to form a partially or fully deuterated alkyl group; halogen and alkyl groups may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl and aryl may combine to form a haloaralkyl.
Further, the anthracene derivative is one of the following CJHB 950-CJHB 1087 structures:
/>
/>
wherein, -T 2 - # is selected from-O-, -S-, or one of the following structures:
* -and-represents a bond.
An organic electroluminescent material comprising said anthracene derivative.
The organic electroluminescent material may be constituted by using the compound of the present invention alone or may contain other compounds at the same time.
The compound of the present invention contained in the organic electroluminescent material of the present invention can be used as, but not limited to, a light emitting layer material, a carrier transporting layer material, or a light refracting layer material.
An organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the anthracene derivative provided by the present invention.
The organic electroluminescent device comprises 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-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, an exciton blocking function can likewise be introduced between the two light-emitting layers. It should be noted, however, that not every one of these layers need be present. The organic electroluminescent device described herein may comprise one light emitting layer, or it may comprise a plurality of light emitting layers. I.e. a plurality of luminescent compounds capable of emitting light are used in the luminescent layer. A system with three light emitting layers is preferred, wherein the three layers can display blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises a compound of the invention according to the invention.
Further, the organic electroluminescent device according to the present 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 anode and/or the light emitting layer is directly adjacent to the electron transport layer or electron injection layer or cathode.
In the other layers of the organic electroluminescent device according to the invention, in particular in the hole injection and hole transport layers and in the electron injection and electron transport layers, all materials can be used in the manner generally used according to the prior art. A person of ordinary skill in the art will thus be able to use all materials known in relation to organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Furthermore, organic electroluminescent devices are preferred, which apply one or more layers by means of a sublimation method, wherein the material is applied by vapor deposition in a vacuum sublimation device at an initial pressure of less than 10 -5 Pa, preferably less than 10 -6 Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa.
Also preferred are organic electroluminescent devices which apply one or more layers by means of an organic vapor deposition process or by means of carrier gas sublimation, wherein the material is applied at a pressure of between 10 -5 Pa and 1 Pa. A particular example of this method is the organic vapor jet printing method, wherein the material is applied directly through a nozzle and is thus structured.
Furthermore, organic electroluminescent devices are preferred in which one or more layers are produced from a solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexography, lithography, photoinitiated thermal imaging, thermal transfer, inkjet printing or nozzle printing. Soluble compounds the soluble compounds are obtained, for example, by suitable substitution of the compounds of formula I. These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, a hybrid method is possible, in which one or more layers are applied, for example from a solution, and one or more further layers are applied by vapor deposition.
These methods are generally known to those of ordinary skill in the art and they can be applied to the organic electroluminescent element comprising the compound according to the present invention without inventive effort.
The invention therefore also relates to a method for manufacturing an organic electroluminescent device according to the invention, which applies at least one layer by means of a sublimation method and/or at least one layer by means of an organic vapour deposition method or by means of carrier gas sublimation and/or at least one layer from a solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to a pharmaceutical composition comprising at least one compound of the invention as indicated above. The same preferences as indicated above in relation to the organic electroluminescent device apply to the compounds of the invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires preparations of the compounds according to the invention. These formulations may be, for example, solutions, dispersions or emulsions. For this purpose, it may be preferable to use a mixture of two or more solvents. Suitable and preferred solvents are, for example, toluene, anisole, o-xylene, m-xylene or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl, 1,2,3, 5-tetramethylbenzene, 1,2,4, 5-tetramethylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxyethanol, 2-pyrrolidone, 3-methylanisole, 4-methylanisole, 3, 4-dimethylbenzene, 3, 5-dimethylbenzene, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decalin, dodecylbenzene, ethyl benzoate, indane, methyl benzoate, 1-methylpyrrolidone, p-cymene, phenetole, 1, 4-diisopropylbenzene, dibenzyl ether, diethylene glycol methyl ether, triethylene glycol butyl methyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol, triethylene glycol, 1, 2-dimethyl benzene ether, 1-dimethyl-n-butyl ether, 1-dimethyl-butyl benzene, 1-dimethyl-n-butyl benzene, 1-dimethyl-butyl benzene, n-butyl benzene, dimethyl benzene, n-butyl benzene, dimethyl benzene, or a mixture of these solvents.
Further, the organic layer is selected from one or more of an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer and a light emitting layer.
Further, the electron-transporting layer and the light-emitting layer contain the anthracene derivative of the present invention.
Further, the light-emitting layer comprises a dopant and a light-emitting host, wherein the dopant comprises a material selected from the group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene, and combinations thereof,Benzanthracene, fluorene, spirofluorene and pentacene and derivatives thereof; the light-emitting host comprises the anthracene derivative of the present invention.
Further, the mass ratio of the dopant to the light-emitting main body is 1:99-50:50.
A consumer product made from the organic electroluminescent device, the consumer product comprising the organic electroluminescent device provided by the invention.
The consumer product described in the present invention may be one of the following products: flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cellular telephones, tablet computers, tablet handsets, personal Digital Assistants (PDAs), wearable devices, laptop computers, digital cameras, video cameras, viewfinders, micro-displays with a diagonal of less than 2 inches, 3-D displays, virtual reality or augmented reality displays, vehicles, video walls comprising a plurality of displays tiled together, theatre or gym screens, phototherapy devices, and billboards.
Unless otherwise indicated, all starting materials used in the present invention are commercially available, and any ranges recited herein include any number between the endpoints and any subrange formed by any number between the endpoints or any number between the endpoints.
Compared with the prior art, the invention has the beneficial effects that:
The anthracene derivative has a novel organic electroluminescent compound with a large steric hindrance non-planar structure formed by anthracene and fluorene, fluorene or spirobifluorene anthracene derivative increases molecular steric hindrance, prevents the generation of an organic intermolecular excitation-excitation compound, improves internal quantum efficiency, and has a shorter luminescence wavelength compared with the existing compound, thereby improving the efficiency and the service life of an organic electroluminescent device containing the compound; in addition, the compound improves the solubility in a solution to solve the problems of productivity and cost of the process of the conventional blue light material, and can be used for preparing a light-emitting layer not in the vapor deposition process but in the solution process in the original process.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, a light emitting layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the layers described.
Fig. 2 shows a schematic diagram of an organic light emitting device 200 with two light emitting layers. The device includes a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first emissive layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second emissive layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213. The device 200 may be prepared by sequentially depositing the layers described. Because the most common OLED device has one light emitting layer, and device 200 has a first light emitting layer and a second light emitting layer, the light emitting peaks of the first and second light emitting layers may be overlapping or cross-overlapping or non-overlapping. In the corresponding layers of device 200, materials similar to those described with respect to device 100 may be used. Fig. 2 provides one example of how some layers may be added from the structure of device 100.
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 will be apparent that the described embodiments are only some, but not all, embodiments of the invention. All other embodiments, based on the examples herein, which are within the scope of the invention as defined by the claims, will be within the scope of the invention as defined by the claims.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the disclosure and percentages such as percentages by mass unless otherwise indicated. The novel series of organic compounds provided by the present invention, all of which are carried out under well known suitable conditions, involve some simple organic preparation, for example the preparation of phenylboronic acid derivatives, can be synthesised by skilled operating skills and are not described in detail in the present invention.
The following examples are examples of the test apparatus and method for testing the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing using a spectral scanner PhotoResearch PR-715;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: the NEWPORT 1931-C test was used;
life test: LTS-1004AC life test apparatus was used.
Example 1
Preparation of intermediate A1:
The preparation method of the intermediate A1 comprises the following steps:
the first step: preparation of Compound Int-1
Under the protection of nitrogen, 50.0mmol of 4-bromo-9, 9-dimethyl spirobifluorene is dissolved in 100mL of dry tetrahydrofuran, the temperature is reduced to 0 ℃,50.0mmol of potassium tert-butoxide is added, the temperature is reduced to-78 ℃, 20.8mL of 2.5M N-butyllithium N-hexane solution is added dropwise, the mixture is stirred and reacted for 10 minutes, 55.0mmol of 2-bromobenzyl chloride solution dissolved in THF is added dropwise, the mixture is stirred and reacted for 2 hours at room temperature, 50mL of 2N diluted hydrochloric acid aqueous solution is added, the mixture is extracted by ethyl acetate, the organic phase is collected, dried, filtered, the filtrate is concentrated to dryness under reduced pressure, and the intermediate Int-1 is obtained by separation and purification by a silica gel column, the yield: 84%.
And a second step of: preparation of Compound Int-2
Dissolving 50.0mmol of the intermediate Int-1 prepared in the first step in 120mL of dry THF, cooling to-78 ℃ under the protection of nitrogen, dropwise adding 22.0mL of 2.5M N-butyllithium N-hexane solution, stirring for reaction for 20 minutes, dropwise adding 75.0mmol of benzonitrile, heating to room temperature, stirring for reaction for 1 hour, adding 50mL of 2N diluted hydrochloric acid aqueous solution, separating an organic phase, extracting the aqueous phase with dichloromethane, collecting an organic phase, drying and filtering, concentrating and drying a filtrate under reduced pressure, separating and purifying by using a silica gel column to obtain Int-2, yellow solid, and obtaining the yield: 87%.
And a third step of: preparation of Compound Int-3
Under the protection of nitrogen, 40.0mmol of intermediate Int-2 is dissolved in 80mL of glacial acetic acid, 0.2mol of 33% hydrogen bromide acetic acid solution is added, the mixture is stirred at room temperature for reaction for 1 hour, the mixture is concentrated to dryness under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain intermediate Int-3, and the yield is: 85%.
Fourth step: preparation of Compound A1
20.0Mmol of intermediate Int-3 is dissolved in 100mL of dichloromethane, the temperature is reduced to 0 ℃ by an ice-water bath, 2.0mmol of p-toluenesulfonic acid is added, 22.0mmol of NBS is added in portions, the mixture is stirred and reacted for 2 hours, 50mL of 10% sodium bicarbonate aqueous solution is added, an organic phase is separated, water washing is carried out, the organic phase is collected, drying and filtration are carried out, the filtrate is concentrated to dryness under reduced pressure, and separation and purification are carried out by a silica gel column, thus obtaining intermediate A1 with the yield of 96%.
Referring to the above synthesis method, the products shown in table 1 were prepared.
TABLE 1 correspondence between reactants and synthetic products
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/>
/>
/>
/>
Example 2
Preparation of Compound CJHB 960:
15.0mmol of intermediate A6 is taken and mixed with 60mL of toluene, 18.0mmol of phenylboronic acid, 54.0mmol of anhydrous sodium carbonate and 173.0mg of Pd (PPh 3)4 catalyst, 30mL of ethanol and 30mL of water are added under the protection of nitrogen, the mixture is heated to reflux and stirred for reaction for 12 hours, cooled to room temperature, filtered, and filter cakes are washed with water and ethanol and separated and purified by a silica gel column to obtain yellow solid CJHB960, the yield is 86%, and MS (MALDI-TOF) is m/z 695.2677[ M+H ] +.
Referring to the above synthesis method, the products shown in table 2 were prepared.
TABLE 2 Table 2 correspondence between reactants and synthetic products and yields
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/>
/>
/>
/>
/>
/>
Wherein, -T 2 - # is selected from-O-, -S-, or one of the following structures:
Example 3
As shown in FIG. 1, the preparation method of the OLED element comprises the following steps:
1) The glass substrate coated with the ITO conductive layer is subjected to ultrasonic treatment in a cleaning agent for 30 minutes, rinsed in deionized water, subjected to ultrasonic treatment in an acetone/ethanol mixed solvent for 30 minutes, baked in a clean environment until completely dried, irradiated by an ultraviolet light cleaning machine for 10 minutes, and bombarded on the surface by a low-energy cation beam.
2) Placing the processed ITO glass substrate into a vacuum chamber, vacuumizing to 1× -5～9×10-3 Pa, evaporating metallic silver on the ITO film as anode, and evaporating film thickness to beContinuing to evaporate the compounds DNTPD and F4TCNQ respectively as hole injection layers, wherein F4TCNQ is 3% of the DNTPD by mass, and the evaporation film thickness is/>Continuously evaporating NPD as a hole transport layer on the hole injection layer film, wherein the evaporation film thickness is/>
3) Continuously evaporating a layer of compound HT202 as electron blocking layer on the hole transport layer to obtain an evaporating film with a thickness of
4) Continuously evaporating an anthracene derivative shown in the formula I and BD025 serving as an organic light-emitting layer on the electron blocking layer, wherein BD025 is a doping material and the anthracene derivative shown in the formula (I) is a main body material, the doping concentration of the compound shown in the formula (I) in the BD025 is 10%, and the evaporation film thickness is
5) Evaporating a layer of compound LiQ and ET210 on the light-emitting layer to obtain an electron transport layer, wherein the mass ratio of LiQ to ET210 is 1:1, and the film thickness is
6) Evaporating a layer of compound LiF on the electron transport layer to obtain an electron injection layer with a thickness ofFinally, metal magnesium and silver are evaporated on the electron injection layer to form a cathode layer of the element, wherein the mass ratio of the magnesium to the silver is 1:10, and the evaporated film thickness is/>
The structure of the compound used in example 3 above is as follows:
comparative example 1
The same procedure as in example 3 was followed except that compound B01 was used instead of the anthracene derivative represented by formula (I). The structure of compound B01 is:
Comparative example 2
The same procedure as in example 3 was followed except that compound B02 was used instead of the anthracene derivative represented by formula (I). The structure of compound B02 is:
comparative example 3
The same procedure as in example 3 was followed except that compound B03 was used instead of the anthracene derivative represented by formula (I). The structure of compound B03 is:
The driving voltage and current efficiency of the organic electroluminescent elements prepared in example 3 and comparative example 1, comparative example 2 and comparative example 3 and the lifetime of the elements were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was increased at a rate of 0.1V per second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent element reached 1000cd/m 2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency; LT90% life test is as follows: the time, in hours, for which the luminance decay of the organic electroluminescent element was 900cd/m 2 was measured using a luminance meter at a luminance of 1000cd/m 2 with a constant current. All results are summarized in table 3, and all results are reported as relative values normalized to the results of comparative example 1.
TABLE 3 results of testing the performance of the components
As can be seen from table 3, the compound of the present invention provides a blue organic electroluminescent element as a blue light material, and the driving voltage of the element is reduced, the current efficiency is improved, and the LT90% lifetime is also improved.
The compound B01 in comparative example 1, the compound B02 in comparative example 2, and the compound B03 in comparative example 3 are different from the compounds of the present invention in that dimethylfluorene or dimethylsilofluorene has a weak planar conjugation ability, is unbalanced in hole and electron transport, and has a stronger hole accepting ability than electron accepting ability, and such imbalance in transport affects exciton formation in the light emitting layer, resulting in high voltage, lower efficiency, and reduced lifetime. The structure of the compound provided by the invention with spirofluorenyl is an orthogonal structure, the steric hindrance is large, and the formation of anthracene derivative fluorescent molecule excimer is reduced, so that the compound has excellent performance in molecular film formation and charge transmission, the charge transmission in the element is more balanced, and the element performance is improved.
The organic electroluminescent device of the present invention can be applied to flat-panel light emitters such as wall-mounted televisions, flat-panel displays, and lighting, light sources such as copiers, printers, backlights for liquid crystal displays, and measuring instruments, display panels, and marker lamps.
The foregoing is merely illustrative of the present invention, and the present invention is not limited thereto, and any person skilled in the art will readily recognize that variations or substitutions are within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.

Claims (10)

1. An anthracene derivative is characterized in that the structural general formula of the anthracene derivative is shown as a formula (I) or a formula (II):
wherein each of the X 1～X8 is N or CH; r 1、R2 is hydrogen; ar 1、Ar2 is each independently selected from the group consisting of hydrogen, deuterium, an aromatic or aromatic ring system having 6 to 60 carbon atoms, or a heteroaromatic or heteroaromatic ring system having 2 to 60 carbon atoms; ar 3、Ar4 is each independently selected from the group consisting of aromatic or aromatic ring systems having 6 to 60 carbon atoms.
2. The anthracene derivative according to claim 1, wherein the heteroaromatic or heteroaromatic ring system is a group consisting of groups represented by II-1 to II-17 and aromatic rings or aromatic ring systems, the specific structure of II-1 to II-17 being as follows:
Wherein each Z 1、Z2 is independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazino, hydrazone, carboxyl or carboxylate thereof, sulfonate or sulfonate thereof, phosphate or phosphate thereof, C 1-C40 alkyl, C 2-C40 alkenyl, C 2-C40 alkynyl, C 1-C40 alkoxy, C 3-C40 naphthene, C 3-C40 cycloalkenyl, substituted or unsubstituted C 6-C60 aryl, substituted or unsubstituted C 6-C60 aryloxy, substituted or unsubstituted C 6-C60 arylthio, or substituted or unsubstituted C 2-C60 heteroaryl;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
t 1 represents an oxygen atom or a sulfur atom;
represents the bond between the substituent and the main structure.
3. The anthracene derivative according to claim 1, wherein the anthracene derivative is one of the following CJHB950 to CJHB1087 structures:
wherein-T 2 -is selected from-O-, S-, or one of the following structures:
* -and- (x) represents a bond.
4. An organic electroluminescent material, characterized in that the organic electroluminescent material comprises the anthracene derivative according to any one of claims 1 to 3.
5. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the anthracene derivative according to any one of claims 1-3.
6. The organic electroluminescent device according to claim 5, wherein the organic layer is one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, and a light emitting layer;
7. The organic electroluminescent device according to claim 6, wherein the electron transporting layer and the light emitting layer comprise the anthracene derivative according to any one of claims 1 to 3.
8. The organic electroluminescent device according to claim 6, wherein the light-emitting layer comprises a dopant and a light-emitting host, the dopant comprising a material selected from the group consisting of anthracene, naphthalene, anthracene, pyrene, perylene, phenanthrene, fluoranthene,Benzanthracene, fluorene, spirofluorene and pentacene and derivatives thereof; the light-emitting host comprises the anthracene derivative according to any one of claims 1 to 3.
9. The organic electroluminescent device of claim 8, wherein the mass ratio of dopant to light-emitting host is 1:99-50:50.
10. A consumer product comprising an organic electroluminescent device as claimed in any one of claims 5 to 9.
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CN112794804A (en) * 2019-11-14 2021-05-14 石家庄诚志永华显示材料有限公司 Spirofluorene derivative and application thereof
CN113429302A (en) * 2021-08-27 2021-09-24 北京八亿时空液晶科技股份有限公司 Naphthofluorene derivative, luminescent material, luminescent element and consumer product

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