CN114890996B - Heterocyclic compound and organic light-emitting element comprising same - Google Patents

Heterocyclic compound and organic light-emitting element comprising same Download PDF

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CN114890996B
CN114890996B CN202210608100.7A CN202210608100A CN114890996B CN 114890996 B CN114890996 B CN 114890996B CN 202210608100 A CN202210608100 A CN 202210608100A CN 114890996 B CN114890996 B CN 114890996B
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organic electroluminescent
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CN114890996A (en
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曹建华
姜卫东
张九敏
边坤
戴雄
邸庆童
何连贞
姜坤
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Beijing Bayi Space LCD Technology Co Ltd
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Beijing Bayi Space LCD Technology Co Ltd
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Priority to PCT/CN2023/095029 priority patent/WO2023231795A1/en
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Abstract

The invention relates to the technical field of organic electroluminescent materialsDomain, in particular to a heterocyclic compound and application thereof. The structural formula of the compound is shown as a formula (I); the compound shown in the formula (I) has a hetero atom joint phenanthrene structure, and can obviously reduce the driving voltage, improve the luminous efficiency and prolong the service life when being applied to an organic electroluminescent element,

Description

Heterocyclic compound and organic light-emitting element comprising same
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a heterocyclic compound and application thereof in an organic light-emitting element.
Background
In general, an organic light emitting phenomenon refers to a phenomenon that emits light when electric energy is applied to an organic substance; that is, when an organic layer is disposed between an anode and a cathode, if a voltage is applied between the two electrodes, holes are injected from the anode to the organic layer, and electrons are injected from the cathode to the organic layer; when the injected holes and electrons meet, excitons are formed, and when the excitons transition to a ground state, light and heat are emitted.
In recent years, organic electroluminescent display technology has tended to mature, and some products have entered the market, but in the industrialization process, many problems still remain to be solved. In particular, various organic materials for manufacturing elements, which have carrier injection and transport properties, material electroluminescent properties, service life, color purity, matching between various materials and between various electrodes, and the like, have not been solved; especially, the luminous efficiency and the service life of the light Emitting element do not meet the practical requirements, which greatly limits the development of organic light-Emitting Diode (OLED) technology. While the metal complex phosphorescent material using triplet light emission has high light emission efficiency, its green and red light materials have reached the use requirements, but the metal complex phosphorescent material requires a phosphorescent material having a high triplet energy level or a hole material to match it. Therefore, the development of phosphorescent materials or hole materials having high triplet energy levels is an urgent need for the development of current OLEDs.
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 elements and in terms of thermal stability during sublimation.
In view of this, the present invention has been made.
Disclosure of Invention
In order to overcome the above-described problems of the conventional techniques and to further improve the characteristics of the organic electroluminescent element, development of a more stable and effective substance that can be used as a phosphorescent material or a hole material in the organic electroluminescent element has been continuously demanded.
The invention aims to provide a heterocyclic compound which can improve the thermal stability of materials and the capacity of transporting carriers, and an organic electroluminescent element prepared by the compound can obviously reduce driving voltage, improve luminous efficiency and prolong service life; it is a further object of the present invention to provide the use of the compounds.
Specifically, the invention provides the following technical scheme:
the invention provides a heterocyclic compound, the structural formula of which is shown as the formula (I):
wherein,
L 1 and L 2 Identical to each otherOr different, each independently selected from single bond, substituted or unsubstituted C 6 -C 60 Arylene, or substituted or unsubstituted C 2 -C 60 A heteroarylene group;
X 1 、X 2 、X 3 each independently is N or CR 3 ，X 1 、X 2 、X 3 At least one of which is N;
y is selected from O, S, CR 4 R 5 、SiR 4 R 5 Or NAr 4 ；
R 1 、R 2 、R 3 、R 4 、R 5 When present, are identical or different and are selected from the group consisting of hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 1 -C 40 Alkoxy, C 2 -C 40 Alkenyl, C 1 -C 40 Alkylthio, C 1 -C 40 Alkoxy, C 3 -C 40 Cycloalkyl, C 1 -C 40 Alkyl sulfoxide group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 6 -C 60 Aryl sulfoxide group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
Ar 2 、Ar 3 、Ar 4 each independently selected from the group consisting of substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Condensed ring aryl, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
Ar 1 selected from the group consisting of groups represented by the following formulas a to h,
in the formulae a to h, T 1 、T 2 Is directly bonded, or is independently selected from O, S, NAr, C (R) 2 Or no T 1 The method comprises the steps of carrying out a first treatment on the surface of the Ar is a substituted or unsubstituted aryl group; r are identical or different from each other and are selected from hydrogen, deuterium, fluorine, hydroxyl, nitrile, nitro, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 1 -C 40 Alkoxy, C 2 -C 40 Alkenyl, C 1 -C 40 Alkylthio, C 1 -C 40 Alkoxy, C 3 -C 40 Cycloalkyl, C 1 -C 40 Alkyl sulfoxide group, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 6 -C 60 Aryl sulfoxide group, substituted or unsubstituted C 3 -C 40 Silyl, substituted or unsubstituted boron, substituted or unsubstituted amine, substituted or unsubstituted aryl phosphine, substituted or unsubstituted phosphine oxide, or substituted or unsubstituted C 2 -C 60 The heterocyclic aryl groups may optionally be joined or fused to form a substituted or unsubstituted ring with or without N, O, S, P, B or C (R) in the ring formed 2 ；
The substituent R is one or more to saturated substitutions;
* -represent L 1 And a moiety bonded to the group represented by formulas a to h.
Preferably, the R 1 、R 2 、R 3 、R 4 、R 5 Each occurrence is independently selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, carbazole, dibenzofuran, or dibenzothiophene.
As a best effortOptionally, the Ar 2 、Ar 3 、Ar 4 Each independently selected from the group consisting of: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, benzine, terphenyl, tetrabiphenyl, triphenylene, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, trimeric indene, heterotrimeric indene, spiro-trimeric indene, spiro-heterotrimeric 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, naphthazole, 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, 5-tetrazine, 1,2, 5-tetrazine, purine, pteridine, indolizine, quinazoline and benzothiadiazole, or a combination of groups derived from these.
Preferably, the Ar 1 Selected from any one of the groups represented by the following formulas 2 to 33,
in formulas 2 to 33, ar is phenyl, naphthyl, anthryl, phenanthryl, pyrenyl, biphenyl, terphenyl, triphenylenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothienyl, carbazolyl, pyridinyl, or a group derived from a combination of these systems; r are identical or different from each other and are selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, phenyl, biphenyl, fluorenyl, two or more adjacent R groups may be optionally joined or fused to form a substituted or unsubstituted ring, with or without N, O, S, P, B or C (R) in the formed ring 2 ；
The substituent R is one or more to saturated substitutions;
* -represent L 1 The site to which the group represented by formula 2 to formula 33 is bonded.
According to an embodiment of the invention, the Ar 1 Selected from any one of the groups shown below,
wherein Ar is phenyl, naphthyl, phenanthryl, biphenyl, terphenyl, triphenylene, fluorenyl, spirobifluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl, pyridinyl, or groups derived from combinations of these systems; r is the same or different from each other and is selected from the group consisting of hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, phenyl, biphenyl, fluorenyl;
the substituent R is one or more to saturated substitutions;
* -represent L 1 The site of attachment to the indicated group.
Preferably, in the above compound, the L 1 、L 2 Each independently selected from the group consisting of groups represented by III-1 through III-15:
wherein,
Z 11 、Z 12 each independently selected from the group consisting of hydrogen, deuterium hydrogen, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or carboxylate thereof, sulfonic acid or sulfonate thereof, phosphoric acid or phosphate thereof, C 1 -C 40 Alkyl, C 2 -C 40 Alkenyl, C 2 -C 40 Alkynyl, C 1 -C 40 Alkoxy, C 3 -C 40 Naphthene radical, C 3 -C 40 Cycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 A group consisting of heteroaryl groups;
Z 13 represents substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Aryl sulfide group, or substituted or unsubstituted C 2 -C 60 One or more of the heterocyclic aryl groups;
y1 represents an integer of 1 to 4; y2 represents an integer of 1 to 6; y3 represents an integer of 1 to 3; y4 represents an integer of 1 to 5;
T 3 represents an oxygen atom or a sulfur atom;
represents the bond between the substituent and the main structure.
In the present invention, the term "substituted or unsubstituted" means that the compound is selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, and ammoniaA group, amidino group, hydrazine group, hydrazone group, carboxyl group or carboxylate thereof, sulfonic acid group or sulfonate thereof, phosphoric acid group or phosphate thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 3 -C 60 Cycloalkyl, C 3 -C 60 Cycloalkenyl, C 6 -C 60 Aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Aryl sulfide group and C 2 -C 60 More than 1 substituent in the heterocyclic aryl group is substituted or unsubstituted, or a substituent which is formed by connecting more than 2 substituents in the above exemplified substituents is substituted or unsubstituted.
Preferably, the compound is selected from the group consisting of compounds represented by the following formulas CJHM383-CJHM 470:
the invention also provides an organic electroluminescent material, which comprises the heterocyclic compound; the organic electroluminescent material comprising the compound of the present invention has the ability of carrier transport.
The invention also provides application of the heterocyclic compound in preparation of an organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layer or the capping layer includes the heterocyclic compound described above.
The organic electroluminescent element 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. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred is a system with three light-emitting layers, 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 the heterocyclic compound of the present invention according to the present invention.
Further, the organic electroluminescent element 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 electron blocking layer or hole transport 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 element 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, preference is given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process, wherein the sublimation process is carried out in a vacuum at a temperature of less than 10 -5 Pa, preferably below 10 -6 The material is applied by vapor deposition at an initial pressure of Pa. However, the initial pressure may also be even lower, for example below 10 -7 Pa。
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 at 10 -5 The material is applied at a pressure between Pa and 1 Pa. A particular example of this method is an 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 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 element according to the invention, at least one layer being applied by means of a sublimation method, and/or characterized in that at least one layer is applied by means of an organic vapour deposition method or by means of carrier gas sublimation, and/or in that at least one layer is applied from solution by spin coating or by means of a printing method.
Furthermore, the present invention relates to heterocyclic compounds comprising at least one of the above-indicated invention. 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 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 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-dimethylanisole, 3, 5-dimethylanisole, acetophenone, alpha-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohexylbenzene, decahydronaphthalene, 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.
Preferably, the organic layer includes a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
The invention also provides a consumer product comprising the organic electroluminescent element.
In addition, unless otherwise specified, all raw materials used in the present invention are commercially available, and any ranges recited in the present invention include any numerical value between the end values and any sub-range constituted by any numerical value between the end values or any numerical value between the end values.
The beneficial effects obtained by the invention are as follows:
the heterocyclic compound shown in the formula (I) has high triplet state energy level, increases the rigidity of phenanthrene or azaphenanthrene molecules, improves the thermal stability of materials and the capability of transporting carriers, and can obviously reduce driving voltage, improve luminous efficiency and prolong service life when being applied to an organic electroluminescent element.
Drawings
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
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
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.
The experimental methods used in the following examples are conventional methods unless otherwise specified. The experimental materials and related equipment used in the examples below, unless otherwise specified, are all commercially available, and the percentages, such as the percentages without otherwise specified, are all mass percentages.
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: photoresearch PR-715 was tested using a spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: NEWPORT 1931-C test was used.
Examples
The synthetic route for compound formula (I) is as follows:
wherein X represents I, br, cl or OTf; the other symbols used are as defined above.
Example 1
A process for the preparation of compound CJHM387 comprising the steps of:
the first step: preparation of intermediate Int-1
20.0mmol of SM-1 (reactant 1) is dissolved in 60mL of glacial acetic acid, 15.4mmol of potassium iodate and 26.2mmol of potassium iodide are added under the protection of nitrogen, the mixture is heated to reflux and stirred for reaction for 2 hours, the reaction temperature is reduced to room temperature, the reaction product is filtered, a filter cake is washed by water and saturated sodium bisulfite aqueous solution, and a silica gel column is used for separation and purification, so that white solid Int-1 is obtained, and the yield is 91%.
And a second step of: preparation of intermediate Int-2
10.0mmol of Int-1 was dissolved in 60mL of toluene and under nitrogen protection 11.0mmol of 9-phenylcarbazole-3-boronic acid (reactant 2), 24.0mmol of anhydrous sodium carbonate, 0.01mmol of Pd (PPh) 3 ) 4 The catalyst, 30mL of ethanol and 30mL of water are added, the temperature is raised to reflux and stirring for reaction for 5 hours, the temperature is reduced, 50mL of water is added for dilution, the organic phase is collected by extraction with ethyl acetate, drying, filtration and decompression concentration of the filtrate are carried out, and the yellow solid Int-2 is obtained by separation and purification by a silica gel column, wherein the yield is 82%.
And a third step of: preparation of intermediate Int-3
Under the protection of nitrogen, 20.0mmol of Int-1 is dissolved in 60mL of THF, the temperature is reduced to minus 78 ℃, 9.6mL of 2.5M N-butyllithium N-hexane solution is added dropwise, the mixture is stirred and reacted for 30 minutes, 30.0mmol of trimethyl borate is added dropwise, the mixture is stirred and reacted for 1 hour at room temperature, 100mL of 1N diluted hydrochloric acid aqueous solution is added, EA is used for extraction, the organic phase is dried, filtered, concentrated under reduced pressure and dried, and the mixture is dispersed and filtered by N-hexane to obtain yellow solid Int-3, and the yield is: 83%.
Fourth step: preparation of Compound CJHM387
Under the protection of nitrogen, 12.0mmol of intermediate Int-3, 10.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (reactant 3), 36.0mmol of potassium phosphate hexahydrate and 40mL of toluene are mixed, then 0.01mmol of Pd132 catalyst, 20mL of ethanol and 20mL of water are added, the mixture is heated to reflux and stirred for reaction for 12 hours, cooled to room temperature, 50mL of water is added for dilution, dichloromethane is used for extraction, an organic phase is collected, dried, filtered, the filtrate is concentrated under reduced pressure and dried, and the yellow solid CJHM387 is obtained by separation and purification by a silica gel column, the yield is 85 percent, and MS (MALDI-TOF): m/z=665.2345 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 )：8.53(1H,s)；8.36～8.32(4H,m)；8.15～8.13(2H,d)；8.07～8.05(2H,d)；7.98～7.90(3H,m)；7.76～7.75(1H,d)；7.69～7.66(2H,d)；7.64～7.55(3H,m)；7.53～7.48(8H,m)；7.36～7.32(1H,m)；7.16～7.14(1H,m)。
Referring to the above synthetic method, the following compounds shown in table 1 were prepared:
TABLE 1
Example 2
A process for the preparation of compound CJHM399 comprising the steps of:
the first step: preparation of Compound Int-4
20.0mmol of Int-1 is dissolved in 80mL of dry xylene, 20.0mmol of carbazole, 60.0mmol of anhydrous potassium carbonate, 0.2mmol of cuprous iodide and 0.6mmol of N, N' -dimethylethylenediamine are added under the protection of nitrogen, the mixture is heated to reflux and stirred for reaction for 15 hours, cooled to room temperature, filtered, a filter cake is washed by dichloromethane, the filtrate is concentrated to dryness under reduced pressure, and the white solid Int-4 is obtained by separation and purification by a silica gel column, and the yield is 75%.
And a second step of: preparation of Compound Int-5
Referring to the synthesis method of the third step of example 1, only Int-2 of the third step of example 1 was replaced with Int-4 to prepare white solid Int-5 in 78% yield.
And a third step of: preparation of Compound CJHM399
Referring to the fourth step of the synthesis method of example 1, only Int-3 of the fourth step of example 1 was replaced with Int-5, 2-chloro-4, 6-diphenyl-1, 3, 5-triazine was replaced with 2-biphenyl-4-chloro-6-phenyl-1, 3, 5-triazine, and the mixture was separated and purified by silica gel column to obtain a yellow solid CJHM399 with a yield of 78%, MS (MALDI-TOF): m/z=665.2355 [ m+h ]] + ； 1 HNMR(δ、CDCl 3 ): 8.54 (1H, s); 8.38 to 8.35 (3H, m); 8.18 to 8.14 (2H, m); 8.05 to 8.02 (2H, m); 7.95 to 7.91 (3H, m); 7.76 to 7.68 (5H, m); 7.58 to 7.54 (2H, m); 7.52 to 7.45 (6H, m); 7.43 to 7.35 (2H, m); 7.18 to 7.14 (2H, m). Referring to the above synthetic method, the following compounds shown in table 2 were prepared:
TABLE 2
Example 3
As shown in fig. 1, the OLED element of the present embodiment is a top-emission light element, and includes a substrate 101, an anode layer 102 disposed on the substrate 101, a hole injection layer 103 disposed on the anode layer 102, a hole transport layer 104 disposed on the hole injection layer 103, an electron blocking layer 105 disposed on the hole transport layer 104, an organic light emitting layer 106 disposed on the electron blocking layer 105, an electron transport layer 107 disposed on the organic light emitting layer 106, an electron injection layer 108 disposed on the electron transport layer 107, a cathode layer 109 disposed on the electron injection layer 108, and a capping layer 110 disposed on the cathode 109, wherein the method for preparing the OLED element includes 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 above ITO glass substrate in vacuum chamber, and vacuumizing to 1×10 -5 ～9×10 -3 Pa, depositing metallic silver as anode layer on the anode layer film, the thickness of deposited film isContinuing to vapor-deposit the compounds 2-TNATA and F4TCNQ as hole injection layers respectively, wherein F4TCNQ is 3% of the mass of 2-TNATA, and the vapor-deposited film thickness is +.>
3) Continuously evaporating a compound HTM101 as a hole transport layer on the hole injection layer to obtain an evaporated film thickness of
4) Continuously evaporating compound EBL as electron blocking layer on the hole injection layer to obtain an evaporating film thickness of
5) The compound of the invention is a main material and GD03 is a doping material, the GD03 is 3% of the mass of the formula (I) and is used as an organic light-emitting layer of the element, and the film thickness of the organic light-emitting layer obtained by evaporation is
6) Continuously evaporating a layer of LiQ and ET01 as electron transport layers of the element on the organic light-emitting layer, wherein ET01 is 50% of LiQ by mass, and the evaporating film thickness is
7) Continuously evaporating a LiF layer on the electron transport layer to form an electron injection layer with an evaporating film thickness of
8) Evaporating metal magnesium and silver on the electron injection layer to form a transparent cathode layer of the element, wherein the mass ratio of magnesium to silver is 1:10, and the film thickness of the evaporated film is
9) Evaporating an NPD CPL layer as element on the transparent cathode layer to obtain an evaporation film with a thickness ofThe OLED element provided by the invention is obtained.
The structure of the compound used in example 3 above is as follows:
example 4
An organic electroluminescent device 200, the structure of which is shown in fig. 2, comprises a substrate 201, an anode 202, a hole injection layer 203, a hole transport layer 204, a first luminescent layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, a hole transport layer 209, a second luminescent layer 210, an electron transport layer 211, an electron injection layer 212, and a cathode 213.
Comparative example 1
By following the same procedure as in example 3, substituting the compound of formula I in step 5) with HS01, comparative element 1 is obtained;
comparative example 2
By following the same procedure as in example 3, substituting the compound of formula I in step 5) with HS02, comparative element 2 is obtained;
the organic electroluminescent element prepared by the above process was subjected to the following performance test:
the driving voltage and current efficiency and the lifetime of the organic electroluminescent elements prepared in example 3 and comparative examples 1 and 2 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent element was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; LT90% life test is as follows: at 1000cd/m using a luminance meter 2 The luminance decay of the organic electroluminescent element was measured to be 900cd/m while maintaining a constant current at luminance 2 Time in hours. The data listed in table 3 are relative data compared to comparative element 1.
TABLE 3 Table 3
As can be seen from Table 3, the device prepared from the compound of the present invention has a lower driving voltage than HS01, a significantly improved current efficiency up to as much as 1.2 times that of the comparative device, and a significantly improved LT90% lifetime of the device at the same luminance.
The compound HS01 of comparative example 1 is different from the compound of the present invention in that the single phenanthrene ring has a weak planar conjugation ability, is unbalanced in the transport of holes and electrons, and has a stronger ability to accept holes than electrons, and such a transport imbalance affects the formation of excitons in the light emitting layer, resulting in high voltage, lower efficiency, and reduced lifetime. The compound of the invention introduces hetero atoms such as oxygen, sulfur and the like on the basis of phenanthrene ring, and improves the conjugation capability of the parent nucleus, so that the compound has excellent performance in molecular film formation and charge transmission, more balanced charge transmission in the element and improved element performance.
The compound HS02 of comparative example 2 is different from the compound of the present invention in that HS02 is a unipolar p-type structure, which has a stronger ability to accept holes than electrons, and such imbalance in transport affects the formation of excitons in the light emitting layer, resulting in high voltage, lower efficiency, and reduced lifetime. The compound of the invention forms a p-n bipolar structure after introducing nitrogen-containing heteroaromatic ring, so the compound has excellent performance in molecular film formation and charge transmission, more balanced charge transmission in the element and improved element performance.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.

Claims (6)

1. A heterocyclic compound, wherein the heterocyclic compound is selected from the group consisting of compounds of the formula:
2. an organic electroluminescent material, characterized in that its raw material comprises the heterocyclic compound as described in claim 1.
3. Use of the heterocyclic compound described in claim 1 for producing an organic electroluminescent element.
4. An organic electroluminescent element, characterized in that it comprises: a first electrode, a second electrode, a capping layer, and one or more organic layers disposed between the first electrode and the second electrode; the material of at least one of the organic layer or the capping layer includes the heterocyclic compound described in claim 1.
5. The organic electroluminescent element according to claim 4, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, or an electron blocking layer.
6. A consumer product comprising the organic electroluminescent element of claim 4.
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