CN114014742B - Triarylbenzene derivative, luminescent material, luminescent element and consumer product - Google Patents

Triarylbenzene derivative, luminescent material, luminescent element and consumer product Download PDF

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CN114014742B
CN114014742B CN202111282565.XA CN202111282565A CN114014742B CN 114014742 B CN114014742 B CN 114014742B CN 202111282565 A CN202111282565 A CN 202111282565A CN 114014742 B CN114014742 B CN 114014742B
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organic electroluminescent
triarylbenzene
derivative
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CN114014742A (en
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戴雄
姜坤
曹建华
唐伟
王志杰
谢佩
李程辉
徐先锋
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Shanghai 800 Million Spacetime Advanced Material Co ltd
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Abstract

The invention relates to a triarylbenzene derivative, a luminescent material, a luminescent element and a consumer product, wherein the structural formula of the triarylbenzene derivative is shown as a formula (I), the derivative is suitable for electronic elements, particularly organic electroluminescent devices, and relates to a material for the organic electroluminescent elements, an organic electroluminescent device and electronic equipment containing the compound. The triarylbenzene derivatives of the present invention have very high efficiency and long life when used as a host material for fluorescent or phosphorescent emitters, have high efficiency when used in organic electroluminescent elements, and result in steep current-voltage curves with use and low operating voltages, have high thermal stability, are capable of sublimation without decomposition and residue, and have high oxidation stability.

Description

Triarylbenzene derivative, luminescent material, luminescent element and consumer product
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a triarylbenzene derivative, a luminescent material, a luminescent element and a consumer product.
Background
As early as 1963, pope et al first discovered that the electroluminescence phenomenon (Pope M,Kal lmann H,Magnante P.Electroluminescence in organic crystals[J].Chem.Phys.,1963,38(8):2042-2043.), of the organic compound single crystal anthracene turned on organic electroluminescence (OLED for short) and related studies. Through development for twenty years, the organic light-Emitting (EL) material has comprehensively realized red, blue and green light emission, and the application field is expanded from small molecules to high molecules, metal complexes and other fields.
In recent years, the organic electroluminescent display technology has tended to mature, and some products have entered the market, but in the industrialization time, many problems still need to be solved. In particular, various organic materials for manufacturing devices, which have carrier injection and transport properties, material electroluminescence properties, service life, color purity, matching between various materials and between various electrodes, and the like, have not been solved. Especially, the light emitting element has not reached practical requirements in light emitting efficiency and service life, which greatly limits the development of OLED technology. The metal complex phosphorescence material utilizing triplet state luminescence has high luminous efficiency, and the green light and red light materials of the metal complex phosphorescence material reach the use requirement, but the metal complex has special electronic structural characteristics, so that the blue light material of the metal complex phosphorescence material can not reach the use requirement.
Under current technological development, improvements are still 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 in terms of thermal stability during sublimation.
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 a triarylbenzene derivative, a light emitting material, a light emitting element, and a consumer product, wherein the triarylbenzene derivative is suitable for use in fluorescent or phosphorescent OLEDs, has high thermal stability, and can be sublimated without decomposition and residue.
The first object of the present invention is to provide a triarylbenzene derivative, wherein the structural formula of the triarylbenzene derivative is shown in formula (I):
wherein each R is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a linear alkyl group having C 1～C40, a linear heteroalkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, a branched or cyclic heteroalkyl group having C 3～C40, an alkenyl or alkynyl group having C 2～C40, an aryl group having 5 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, or NR 1R2, and R is not all hydrogen or deuterium;
R 1、R2 are each the same or different and are selected from the group consisting of substituted or unsubstituted aryl of C 5～C60, substituted or unsubstituted arylamine of C 5～C60, substituted or unsubstituted arylboron of C 5～C60, substituted or unsubstituted arylphosphorus of C 5～C60, substituted or unsubstituted heteroaryl of C 2～C60, R 1 and R 2 may optionally be joined or fused to form one or more additional substituted or unsubstituted rings with or without one or more heteroatoms N, P, B, O, S, P =o, or with or without one or more CR 3R4、SiR3R4 in the ring formed;
Ar is selected from the group consisting of a substituted or unsubstituted arylene group of C 5～C60, a substituted or unsubstituted arylene group of C 5～C60, a substituted or unsubstituted arylene borylene group of C 5～C60, a substituted or unsubstituted arylene phosphene group of C 5～C60, and a substituted or unsubstituted heteroarylene group of C 2～C60;
n represents an integer of 0 to 5, preferably n represents an integer of 1 to 3;
R 3、R4 is, identically or differently, selected at each occurrence from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a linear alkyl group having C 1～C40, a linear heteroalkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, a branched or cyclic heteroalkyl group having C 3～C40, an alkenyl or alkynyl group having C 2～C40, an aryl group having from 5 to 60 carbon atoms or a heteroaryl group having from 2 to 60 carbon atoms.
The inventors have found through extensive experimentation that surprisingly said derivatives lead to significant improvements in organic electroluminescent elements, in particular in terms of lifetime, efficiency and operating voltage. In particular, when the compound of the present invention is used as a hole transport material or as a host material, this applies to phosphorescent and fluorescent electroluminescent elements. The materials generally have high thermal stability and are therefore capable of sublimation without decomposition and without residues. The invention thus relates to these materials and to electronic components comprising compounds of this type. Particularly, very good results are obtained with aromatic monoamines, which is a surprising result, since hole transport materials containing at least two nitrogen atoms are often used in organic electroluminescent elements.
Further, the formula (I) is selected from the group consisting of the following formulas (II) to (XII):
Wherein T is selected from O, S, CR 3R4、NR5 or SiR 3R4;
Wherein R 3、R4、R5 is, identically or differently, selected at each occurrence from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, a straight-chain alkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, an aryl group having from 5 to 60 carbon atoms or a heteroaryl group having from 2 to 60 carbon atoms;
the substituent R is 1 substituted to saturated substitution.
Further, the groups R 1 and R 2 are, identically or differently, at each occurrence, selected from the group consisting of groups of formulae (2) to (33):
Wherein R 3、R4、R5 is, identically or differently, selected at each occurrence from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, a straight-chain alkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, an aryl group having from 5 to 60 carbon atoms or a heteroaryl group having from 2 to 60 carbon atoms;
Wherein the dashed key indicates the location of the connection to N.
Further, the group Ar is selected from the group consisting of structures represented by formulas (34) to (58):
Wherein one dashed bond indicates a bond to benzene in the triarylbenzene host and the other dashed bond indicates a bond to N or R;
R 3、R4、R5 is selected identically or differently on each occurrence from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, a straight-chain alkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, an aryl group having from 5 to 60 carbon atoms or a heteroaryl group having from 2 to 60 carbon atoms.
Further, R in the groups (2) to (58) particularly preferably represents hydrogen.
Further, R3 and R4 particularly preferably represent methyl, phenyl or fluorenyl.
Further, the group R5 particularly preferably represents methyl, ethyl, phenyl, naphthyl, phenanthryl, biphenyl, triphenylene.
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; the heteroatom is preferably 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 condensed aryl or heteroaryl group such as anthracene, phenanthrene, benzophenanthrene, quinoline, isoquinoline, anthracidine, and the like. Or from a simple aryl group such as benzene, naphthalene, phenanthrene, pyridine, etc., or combinations of these groups with one or more non-aromatic units such as C, N, O or S atoms, thus, for example, like systems in which two or more aryl groups are linked by, for example, a short alkyl group, such as fluorene, 9' -spirobifluorene, 9-diaryl fluorene, carbazole, diaryl ether, dibenzofuran, dibenzothiophene, etc.
Alkyl in the sense of the present invention contains from 1 to 40 carbon atoms and wherein the individual hydrogen atoms or-CH 2 -groups may also be replaced by the abovementioned radicals R is preferably taken to mean 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, cyclooctenyl, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl, methoxy, trifluoromethoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, sec-pentyloxy, 2-methylbutoxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, cycloheptyloxy, n-octyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2, 2-trifluoroethoxy. Heteroalkyl is preferably alkyl having from 1 to 40 carbon atoms, meaning a radical in which the individual hydrogen atoms or-CH 2 -groups may be replaced by oxygen, sulfur, halogen atoms, is taken to mean alkoxy, alkylthio, fluoroalkoxy, fluoroalkylthio, 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-trifluoroethoxy, 2-trifluoroethylthio, ethyleneoxy, ethylenethio, propyleneoxy, propylenethio, butylenethio, butyleneoxy, pentenyloxy, pentenylthio, cyclopentenyloxy, cyclopentenylthio, hexenyloxy, hexenylthio, cyclohexene thio, acetylenyloxy, acetylenylthio, propynyloxy, butynylthio, pentynyloxy, pentynylthio, hexyloxy, hexylynylthio.
In general, cycloalkyl, cycloalkenyl groups according to the invention may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 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 nitrile groups.
Alkenyl or alkynyl groups according to the invention have 2 to 40 carbon atoms and alkenyl or alkynyl groups in which a separate hydrogen atom may be substituted by the above-mentioned group R are preferably ethenyl, propenyl, butenyl, isobutenyl, styryl, distyryl, ethynyl, propynyl, butynyl, phenylethynyl; in addition, one or more hydrogen atoms may be replaced by deuterium atoms, halogen atoms, or nitrile groups.
Further, aryl or heteroaryl according to the invention refers in particular to groups 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, 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 triarylbenzene derivative includes the following CJHM905,905 to CJHM1006,1006 structures:
the second object of the invention is to provide an organic electroluminescent material comprising the triarylbenzene derivative.
Preferably, the organic electroluminescent material comprises a material of the compound of the invention having a carrier transporting capacity.
A third object of the present invention is to provide an organic electroluminescent element comprising a first electrode, a second electrode, a CPL layer, and at least one organic layer interposed between the first electrode and the second electrode, at least one of the organic layers or the CPL layer comprising the triarylbenzene derivative.
In this case, the above compounds may be used singly or in combination of two or more.
The one or more organic layers may be any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, and an electron injection layer. The organic layer containing the compound of the above chemical formula (I) may preferably be a CPL layer, a light-emitting layer, a hole injection layer, a hole transport layer, and a hole transport auxiliary layer further laminated on the hole transport layer, and more preferably may be a hole injection layer or a CPL layer.
The light-emitting layer of the organic electroluminescent element according to the present invention may contain a host material, preferably a phosphorescent host material, and in this case, as a host material, a compound of the above chemical formula (I) may be contained. When the light-emitting layer contains the compound represented by the above chemical formula (I), the electron transport ability increases, and the binding force between holes and electrons in the light-emitting layer increases, so that an organic electroluminescent element excellent in efficiency (light-emitting efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be provided. The dopant of the light-emitting layer of the organic electroluminescent element of the present invention may contain the compound of the above chemical formula (I), or may contain other compounds as dopants.
The hole injection layer of the organic electroluminescent element of the present invention may contain a hole injection material, and in this case, the compound of the above chemical formula (I) may be contained as the hole injection material. In the case where the hole injection layer contains the compound represented by the above chemical formula (I), the hole injection ability is increased by a deep molecular orbital level, and the driving voltage can be reduced, so that an organic electroluminescent element excellent in efficiency (light emitting efficiency and power efficiency), lifetime, luminance, driving voltage, and the like can be provided. Wherein, CPL layer can be further laminated on the cathode layer of the organic electroluminescent element. In this way, when the CPL layer contains the compound represented by the above chemical formula (I), the light extraction effect is promoted by the high light refractive index, and therefore, especially, the luminance, lifetime, driving voltage, and the like of the blue organic electroluminescent element can be improved.
The structure of the organic electroluminescent element of the present invention is not particularly limited, and as a non-limiting example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially stacked may be used. Wherein, a CPL layer may be further laminated on the cathode layer, as shown in fig. 2. The organic electroluminescent element of the present invention may have a structure in which an insulating layer or an adhesive layer is interposed between the electrode and the organic layer.
On the other hand, in the organic electroluminescent element of the present invention, in addition to one or more layers of the organic layer containing the compound represented by the above chemical formula (I), the organic layer and the electrode can be formed by materials and methods well known in the art.
Further, a substance that can be used as an anode included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, metals such as vanadium, chromium, copper, zinc, gold, aluminum, or the like, or alloys thereof can be used; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); a combination of metals such as Al or SnO2 and Sb and oxides; conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene ] (PEDT), polypyrrole, and polyaniline; and carbon black, etc.
The substance that can be used as the cathode included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead, or alloys thereof can be used; and multilayer structures such as LiF/Al and LiO 2/Al.
The substance that can be used as the substrate included in the organic electroluminescent element according to the present invention is not particularly limited, and as a non-limiting example, a silicon wafer, quartz, a glass plate, a metal plate, a plastic film, a sheet, or the like can be used.
Furthermore, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process, wherein the material is applied by vapor deposition in a vacuum sublimation apparatus 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 elements in which one or more layers are applied by means of an organic vapor deposition process or by means of sublimation of a carrier gas, 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 elements are preferred, from which one or more layers are produced, 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, for example, are obtained by appropriate substitution. 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 element according to the invention, at least one layer being applied by means of a sublimation method and/or at least one layer being applied by means of an organic vapour deposition method or by means of carrier gas sublimation and/or at least one layer being applied from solution by spin coating or by means of a printing method.
Furthermore, the invention relates to a composition comprising at least one of said compounds of formula (I). The same preferable cases as indicated above with respect to the organic electroluminescent element apply to the compound of the present invention. In particular, the compounds may furthermore preferably comprise further compounds. Treatment of the compounds of formula (I) 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-, m-or p-xylene, methyl benzoate, mesitylene, tetralin, o-dimethoxybenzene, tetrahydrofuran, methyltetrahydrofuran, tetrahydropyran, chlorobenzene, dioxane, phenoxytoluene, in particular 3-phenoxytoluene, (-) -fenchyl ketone, 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 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 mixtures of these solvents.
Further, the triarylbenzene derivative is used as a hole transport layer material, a hole injection layer material, an exciton blocking layer material, or a CPL layer material in an organic electroluminescent element.
Further, the hole injection layer or the CPL layer of the organic electroluminescent element contains the organic electroluminescent material.
A fourth object of the present invention is to provide a consumer product comprising said organic electroluminescent element.
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.
Compared with the prior art, the invention has the beneficial effects that:
(1) The triarylbenzene derivative is benzene substituted by 1,2, 4-triaryl by aryl acetylene in one step, has simple preparation and low cost, and simultaneously introduces a substituent with large steric hindrance to ensure that molecules are not easy to crystallize, improve the glass transition temperature and improve the thermal stability of the molecules;
(2) The triarylbenzene derivative is very suitable for being used in a hole injection or hole transport layer in an organic electroluminescent element, and is particularly suitable for a CPL layer, and the triarylbenzene derivative has a lower HOMO energy level, so that the injection of holes is facilitated; the light refractive index is large, but the light absorption coefficient is small, so that the light extraction efficiency is improved;
(3) The triarylbenzene derivatives of the present invention have very high efficiency and long life when used as a hole injection layer material, and are particularly useful when used as a hole injection material together with other doping materials, such as p-type dopants;
(4) The derivatives have a high efficiency when used in organic electroluminescent elements and lead to steep current-voltage curves in the case of use and low operating voltages, have a high thermal stability and can be sublimated without decomposition and residues, in addition to a high oxidation stability, have a positive effect on the handling of the derivatives and on the storage stability of the solutions.
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 is a schematic diagram of a CPL-containing layer of an organic electroluminescent device of the present invention;
fig. 2 is a schematic view of an organic electroluminescent element of the present invention without a hole blocking layer.
Reference numerals
101-Substrate, 102-anode layer, 103-hole injection layer, 104-hole transport layer, 105-electron blocking layer, 106-light emitting layer, 107-hole blocking layer, 108-electron transport layer, 109-electron injection layer, 110-cathode layer, 111-CPL layer.
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 description of the present invention, unless otherwise indicated, the meaning of "a plurality" is two or more; the orientation or positional relationship indicated by the terms "upper", "lower", etc. are based on the orientation or positional relationship shown in the drawings, are merely for convenience of description and to simplify the description, and are not indicative or implying that the apparatus or elements in question must have a specific orientation, be constructed and operated in a specific orientation, and therefore should not be construed as limiting the present invention.
In the invention, the preparation methods are all conventional methods unless otherwise specified. All materials used, unless otherwise indicated, are commercially available from the public disclosure and all percentages, such as by mass, are percentages unless otherwise indicated.
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.
The synthetic route of the triarylbenzene derivative provided by the invention comprises the following steps:
wherein X is selected from hydrogen, chlorine, bromine, iodine or OTf; r, ar and n have the meanings as defined above.
Example 1
The preparation method of the compound A1 comprises the following steps:
110.0mmol of p-chloroacetylene is dissolved in 80.0mL of acetonitrile, 3.3mmol of cobalt iodide, 3.3mmol of potassium tert-butoxide and 11.0mmol of pinacol borane are added under the protection of nitrogen, the temperature is raised to 30 ℃, stirring reaction is carried out for 12 hours, decompression concentration and drying are carried out, and the compound A1 is obtained by separating and purifying by a silica gel column, white solid is obtained, and the yield is: 62%, MS (TOF) m/z=408.0233 [ m + ].
Referring to the synthetic method of A1 above, the following compounds were prepared:
example 2
Preparation of compound CJHM910,910:
36.0mmol of N-phenyl- [1,1' -biphenyl ] -4-amine, 10.0mmol of compound A1, 45.0mmol of sodium tert-butoxide, 0.05mmol of Pd 2(dba)3CHCl3 catalyst, 0.1mL of 10% solution of tri-tert-butyl-phosphorus in toluene and 80mL of xylene are added, the mixture is heated to 110 ℃ under the protection of nitrogen, stirred and reacted for 12 hours, cooled to room temperature, 50mL of water is added for dilution, dichloromethane is used for extraction, the organic phase is dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the filtrate is separated and purified by a silica gel column to obtain compound CJHM as a white solid, the yield of which is 76%, and MS (TOF) m/z=1036.4644 [ M+H ].
Referring to the above-described analogous synthetic methods, the following compounds were prepared:
Example 3
Preparation of compound CJHM 956:
10.0mmol of A2, 35.0mmol of 3-pyridine boric acid, 60.0mmol of potassium carbonate, 0.01mmol of Pd132 catalyst, 40mL of toluene, 20mL of ethanol and 20mL of water are added, the mixture is heated, refluxed and stirred under the protection of nitrogen for reaction for 12 hours, cooled to room temperature, 50mL of water is added for dilution, ethyl acetate is used for extraction, the organic phase is dried, filtered, the filtrate is concentrated and dried under reduced pressure, and the obtained filtrate is separated and purified by a silica gel column to obtain a compound CJHM956, the yield is 87%, and MS (TOF) m/z=538.2301 [ M+H ].
Referring to the above-described analogous synthetic methods, the following compounds were prepared:
Example 4
Preparation of compound CJHM 999:
20.0mmol of A10 is dissolved in 80mL of dichloromethane, 40mL of 30% hydrogen peroxide is added, the temperature is raised, the reflux and stirring reaction is carried out for 10 hours, the cooling is carried out to room temperature, 100mL of water is added for dilution, the dichloromethane is used for extraction, the organic phase is dried, the filtration is carried out, the filtrate is concentrated to dryness under reduced pressure, the silica gel column is used for separation and purification, and the compound CJHM999 is obtained, the white solid is obtained, the yield is 100%, and MS (TOF) m/z=907.2678 [ M+H ].
Example 5
A process for the preparation of compound CJHM1003 comprising the steps of:
the first step: preparation of Compound A11
Under the protection of nitrogen, 20.0mmol of 5, 10-diphenyl-5, 10-dihydrodibenzo [ b, e ] [1,4] azaborane (CAS: 1347741-58-5) is dissolved in 50mL of dry THF, cooled to minus 78 ℃, 22mmol of 0.5M ethynyl magnesium bromide THF solution is dropwise added, stirred at room temperature for reaction for 1 hour, 5mL of methanol is added, concentrated and dried under reduced pressure, 150mL of methanol is added for stirring and dissolving, 22mmol of tetramethyl ammonium chloride solid is added for reaction for 24 hours at room temperature, filtration and filter cake washing with methanol are carried out, thus obtaining the compound A11, and the yield is 46%.
And a second step of: preparation of Compound CJHM1003
10.0Mmol of A11 is dissolved in 60.0mL of acetonitrile, under the protection of nitrogen, 0.2mmol of cobalt iodide, 0.1mmol of potassium tert-butoxide and 1.0mmol of pinacol borane are added, the temperature is raised to 30 ℃ and the mixture is stirred for 12 hours, 40mL of 2N diluted hydrochloric acid is added dropwise, the mixture is extracted with dichloromethane, the organic phase is collected, washed with water, dried and concentrated under reduced pressure, and the mixture is separated and purified by a silica gel column to obtain a compound CJHM1003 which is white solid with the yield: 78%, MS (TOF) m/z=838.3754 [ m+h ].
Referring to the above-described analogous synthetic methods, the following compounds were prepared:
The OLED element provided by the present invention is shown in fig. 1 and fig. 2, and the OLED element provided by the present invention is prepared by taking the structure of the OLED element shown in fig. 2 as an example. In fig. 2, 101 is a substrate, 102 is an anode layer, 103 is a hole injection layer, 104 is a hole transport layer, 105 is an electron blocking layer, 106 is a light emitting layer, 108 is an electron transport layer, 109 is an electron injection layer, 110 is a cathode layer, and 111 is a CPL layer.
Comparative example 1
An organic electroluminescent element was produced as described below using the following compound formula C as a dopant material for the hole injection layer, formula E as a material for the hole injection layer host, formula D as a hole transport layer material, formula H as an electron blocking layer material, formula a as a host material for the light emitting layer, formula B as a dopant material for the light emitting layer, formula G as a dopant material for the electron transport layer, liQ as a host material for the electron transport layer, and formula F as a material for the CPL layer.
Al is added with/E+C(3％)/D/H/A+B(3％)/LiQ+G(30％)/LiF/Mg+Ag(50％)/FThe organic electroluminescent device of comparative example 1 was produced by sequentially vapor-depositing light-emitting devices on ITO glass using an EL vapor deposition machine manufactured by DOV corporation.
Example 6
An organic electroluminescent device was produced in the same manner as in comparative example 1, except that the above-mentioned compound E or F was replaced with the compounds CJHM to CJHM1006 according to the present invention: ITO/Al(Inventive Compounds of formula I) +C (3%)/D/H/A+B(3％)/LiQ+G(30％)/LiF/Mg+Ag(50％)/FOr ITO/Al/E+C(3％)/D/H/A+B(3％)/LiQ+G(30％)/LiF/Mg+Ag(50％)(Compound of the present invention formula I)/>)
The performance of the resulting element was a test result at an element luminance of 1000 nits, and data of voltage, external Quantum Efficiency (EQE), current efficiency (LE), and decay lifetime LT95% were normalized with respect to the element of comparative example 1, and the results are shown in table 1.
TABLE 1 results of component Performance test
As is clear from the above table, the OLED element prepared by using the triarylbenzene derivative of the present invention as the host material of the hole injection layer has low driving voltage, high efficiency, and good color purity, and the LT95% lifetime of the element is greatly improved under the condition that the light-emitting luminance of the element is initially 1000 nits. The OLED element prepared from the triarylbenzene derivative by using the CPL material has higher light emitting efficiency, increased color gamut and more gradual service life.
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 (8)

1. A triarylbenzene derivative, wherein the triarylbenzene derivative is selected from the group consisting of:
Wherein T is selected from O, S, CR 3R4、NR5 or SiR 3R4;
Wherein R 3、R4、R5 is, identically or differently, selected at each occurrence from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, a straight-chain alkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, an aryl group having from 5 to 60 carbon atoms or a heteroaryl group having from 2 to 60 carbon atoms;
Each R is independently selected from the group consisting of a hydrogen atom, a deuterium atom, a halogen atom, a nitrile group, a linear alkyl group having C 1～C40, a linear heteroalkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, a branched or cyclic heteroalkyl group having C 3～C40, an alkenyl or alkynyl group having C 2～C40, an aryl group having 5 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms, or NR 1R2, and R is not all hydrogen or deuterium;
R 1、R2 are each the same or different and are selected from the group consisting of aryl of substituted or unsubstituted C 5～C60, arylamine of substituted or unsubstituted C 5～C60, arylboron of substituted or unsubstituted C 5～C60, arylphosphorus of substituted or unsubstituted C 5～C60, heteroaryl of substituted or unsubstituted C 2～C60, R 1 and R 2 may optionally be joined or fused to form one or more additional substituted or unsubstituted rings with or without one or more heteroatoms N, P, B, O, S, P =o, or with or without one or more CR 3R4、SiR3R4 in the ring formed.
2. The triarylbenzene derivative of claim 1 wherein said groups R 1 and R 2 are, identically or differently, selected from the group consisting of groups of formulae (2) to (33) at each occurrence:
Wherein R 3、R4、R5 is, identically or differently, selected at each occurrence from the group consisting of a hydrogen atom, a deuterium atom, a fluorine atom, a nitrile group, a straight-chain alkyl group having C 1～C40, a branched or cyclic alkyl group having C 3～C40, an aryl group having from 5 to 60 carbon atoms or a heteroaryl group having from 2 to 60 carbon atoms;
Wherein the dashed key indicates the location of the connection to N.
3. The triarylbenzene derivative of any one of claims 1-2, wherein said compound comprises the following CJHM to CJHM structures 1006:
4. An organic electroluminescent material comprising the triarylbenzene derivative as claimed in any one of claims 1 to 3.
5. An organic electroluminescent element comprising a first electrode, a second electrode, a CPL layer, and at least one organic layer interposed between the first electrode and the second electrode, wherein at least one layer or CPL layer of the organic layer comprises the triarylbenzene derivative according to any one of claims 1 to 3.
6. The organic electroluminescent element according to claim 5, wherein the triarylbenzene derivative is used as a hole transport layer material, a hole injection layer material, an exciton blocking layer material, or a CPL layer material in the organic electroluminescent element.
7. The organic electroluminescent element according to claim 6, wherein the hole injection layer or CPL layer of the organic electroluminescent element comprises the material of claim 6.
8. A consumer product comprising the organic electroluminescent element of claim 6 or 7.
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