WO2023241569A1 - Composé d'aza-adamantane et élément électroluminescent organique - Google Patents

Composé d'aza-adamantane et élément électroluminescent organique Download PDF

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WO2023241569A1
WO2023241569A1 PCT/CN2023/099910 CN2023099910W WO2023241569A1 WO 2023241569 A1 WO2023241569 A1 WO 2023241569A1 CN 2023099910 W CN2023099910 W CN 2023099910W WO 2023241569 A1 WO2023241569 A1 WO 2023241569A1
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曹建华
姜卫东
张九敏
王志杰
谢佩
张海威
边坤
戴雄
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上海八亿时空先进材料有限公司
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Definitions

  • the present invention relates to the technical field of organic electroluminescent materials, and in particular to an azaadamantane compound and its application in organic electroluminescent elements.
  • organic luminescence refers to the phenomenon of emitting light when electric energy is applied to an organic substance; that is, when an organic layer is arranged between an anode and a cathode, if a voltage is applied between the two electrodes, holes will be injected from the anode. To the organic layer, electrons are injected from the cathode to the organic layer; when the injected holes and electrons meet, excitons are formed. When the excitons transition to the ground state, they emit light and heat.
  • the object of the present invention is to provide an azaadamantane compound.
  • the organic electroluminescent element prepared by using the azaadamantane compound can significantly reduce the driving voltage, improve the luminous efficiency and life; another object of the present invention is to provide the azaadamantane compound. Applications of heteroadamantane compounds.
  • the present invention provides the following technical solutions:
  • the invention provides an azaadamantane compound, the structural formula of which is shown in formula (I):
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently selected from hydrogen, deuterium, halogen, nitrile, C 1 -C 40 alkyl, C 3 -C 40 cycloalkyl or branched alkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted C 6 -C 60 fused ring aryl, substituted or unsubstituted C 6 - A group consisting of a C 60 arylamine group, a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group, or a group represented by formula (II). Any two or more adjacent substituents are optional. join or fuse to form substituted or unsubstituted rings;
  • Ar 1 and Ar 2 are each independently selected from a C 1 -C 40 alkyl group, a C 3 -C 40 cycloalkyl group or a branched alkyl group, a substituted or unsubstituted C 6 -C 60 aryl group, A group consisting of a substituted or unsubstituted C 6 -C 60 fused ring aryl group, a substituted or unsubstituted C 6 -C 60 arylamine group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group, Ar 1.
  • Ar 2 can be arbitrarily joined or fused to form a substituted or unsubstituted ring;
  • n is selected from an integer from 0 to 5;
  • L 1 is selected from a single bond, a substituted or unsubstituted C 6 -C 60 arylene group, or a substituted or unsubstituted C 2 -C 60 heteroarylene group;
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from hydrogen, deuterium, fluorine, nitrile, methyl, ethyl, tert-butyl base, phenyl, biphenyl, terphenyl, naphthyl, phenanthrenyl, triphenylene, carbazolyl, fluorenyl, dibenzofuran, dibenzothiophene, substituted or unsubstituted C 6 -C 60 Arylamine group, substituted or unsubstituted C 2 -C 60 heterocyclic aryl group, or a group represented by formula (II), and in R 1 , R 2 , R 3 , R 4 , R 5 , At least one of R 6 , R 7 , and R 8 is a group represented by formula (II), or any two or more adjacent substituents may be optionally joined or fused to form a substituted or
  • Ar 1 and Ar 2 are each independently selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl group and a substituted or unsubstituted C 6 -C 60 arylamine group.
  • said m is selected from 0, 1 or 2.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are each independently selected from hydrogen, deuterium, fluorine, nitrile group, substituted or unsubstituted C 6 -
  • the aryl group and heterocyclic aryl group are selected from the group consisting of the following groups: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, aiphenyl, terphenyl, tetraphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydrogen Pyrene, cis or trans indenofluorene, cis or trans indenocarbazole, cis or trans indolocarbazole, trimeric indene, isotrimeric indene, spirotrimeric indene, spiroisotrimeric Indene, furan, benzofuran, isobenzofuran, dibenz
  • the L 1 is selected from a single bond or a group consisting of the following groups III-1 to III-15:
  • Z 11 and Z 12 are each independently selected from hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonic acid Salt, phosphate group or its phosphate, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl group, C 1 -C 60 alkoxy group, C 3 -C 60 cycloalkyl group, C 3 -C 60 cycloalkenyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 aryl sulfide group, or a group consisting of substituted or unsubstituted C 2
  • Z 13 represents a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 aryl sulfide group, or a substituted or unsubstituted C 6 -C 60 aryl sulfide group.
  • T 2 is selected from O, S, CR'R" or NAr';
  • R', R" are each independently selected from hydrogen, deuterium, C 1 -C 60 alkyl group, C 1 -C 60 heteroalkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted A group consisting of C 6 -C 60 arylamine groups, or substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups, R' and R" can optionally be joined or fused to form another one or more Substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R', R" is methyl, phenyl or fluorenyl ;
  • Ar' is selected from C 1 -C 60 alkyl, C 1 -C 60 heteroalkyl, C 3 -C 60 cycloalkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted A group consisting of a C 6 -C 60 fused ring aryl group, a substituted or unsubstituted C 6 -C 60 arylamine group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group; preferably, Ar' is methyl, ethyl, phenyl or naphthyl;
  • the Ar 1 and Ar 2 are selected from the group consisting of the following groups:
  • the hydrogen atom on each substituent may be substituted by a substituent selected from hydrogen deuterium, halogen, hydroxyl, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxyl or its carboxylic acid Salt, sulfonic acid group or its sulfonate, phosphate group or its phosphate, C 1 -C 60 alkyl group, C 2 -C 60 alkenyl group, C 2 -C 60 alkynyl, C 1 -C 60 alkoxy, C 3 -C 60 cycloalkyl, C 3 -C 60 cycloalkenyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or A group consisting of an unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 aryl sulfide group, or a substituted or unsubstituted C 2
  • G is selected from O, S, CR’R” or NAr’;
  • R', R" are each independently selected from hydrogen, deuterium, C 1 -C 60 alkyl group, C 1 -C 60 heteroalkyl group, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted A group consisting of C 6 -C 60 arylamine groups, or substituted or unsubstituted C 2 -C 60 heterocyclic aryl groups, R' and R" can optionally be joined or fused to form another one or more Substituted or unsubstituted rings, containing or not containing one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R', R" is methyl, phenyl or fluorenyl ;
  • Ar' is selected from C 1 -C 60 alkyl, C 1 -C 60 heteroalkyl, C 3 -C 60 cycloalkyl, substituted or unsubstituted C 6 -C 60 aryl, substituted or unsubstituted A group consisting of a C 6 -C 60 fused ring aryl group, a substituted or unsubstituted C 6 -C 60 arylamine group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group; preferably, Ar' is methyl, ethyl, phenyl or naphthyl;
  • the aryl group, condensed ring aryl group or heterocyclic aryl group of the present invention particularly refers to groups derived from the following substances: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, aiphenyl, terphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis Or trans indenofluorene, cis or trans indenocarbazole, cis or trans indolocarbazole, trimer indene, isotrimeric indene, spiro trimer indene, spiro isotrimeric indene, furan, Benzofuran, isobenz
  • substituted or unsubstituted means one selected from the group consisting of hydrogen, deuterium, halogen atom, hydroxyl group, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or its carboxyl group.
  • the aryl sulfide group and the C 2 -C 60 heterocyclic aryl group are substituted or unsubstituted by one or more substituents, or are connected by two or more substituents among the above-exemplified substituents. Superseded or not superseded.
  • the *-NAr 1 Ar 2 is selected from the group consisting of the following formulas B1 to B15:
  • *—G—* is selected from single bond, *—O—*, *—S—* or one of the following structures:
  • Each R 7 in the structure B1 to B15 is independently selected from hydrogen, deuterium, halogen, nitrile group, C 1 -C 40 alkyl group, C 3 -C 40 cycloalkyl group or branched chain alkyl group.
  • the plurality of substituents may be the same or different from each other.
  • the azaadamantane compound is selected from the group consisting of the following D253 to D525:
  • *—T 3 —* is selected from *—O—*, *—S—* or one of the following structures:
  • the present invention also provides a method for preparing the above-mentioned azaadamantane compound, as shown in Scheme 1 to Scheme 2:
  • X 1 , X 2 , and X 3 are H, Cl, Br, I or OTf; R is H, alkyl or aryl; other symbols used are as defined in formula (I),
  • the raw materials for synthesizing the compound represented by formula (I) can be purchased through commercial channels.
  • the principle, operation process, conventional post-treatment, column purification, recrystallization purification and other means are well known to synthetic practitioners in the field and can be Implement the synthesis process and obtain the target product.
  • the compound of formula (I) is prepared from X1- substituted biphenyl through substitution reaction, condensation reaction, SUZUKI coupling and other reactions.
  • the intermediate Ar 1 Ar 2 N-(L) m B(OH) 2 or Ar 1 Ar 2 NH is prepared by palladium-catalyzed or base-catalyzed coupling reaction.
  • a palladium catalyst that can be used for palladium-catalyzed coupling reaction, it can be selected from: Pd(P- t Bu 3 ) 2 , Pd(PPh 3 ) 4 , Pd 2 (dba) 3 , Pd 2 (dba) 3 CHCl 3 , PdCl 2 (PPh 3 ) 2 , PdCl 2 (CH 3 CN) 2 , Pd(OAc) 2 , Pd(acac) 2 , Pd/C, PdCl 2 , [Pd(allyl)Cl] 2, etc., or use two mixture of one or more species.
  • the base used in the palladium-catalyzed coupling reaction or the base-catalyzed coupling reaction can be selected from: sodium tert-butoxide, potassium tert-butoxide, sodium hydride, lithium hydride, sodium tert-amyloxide, sodium ethoxide, sodium methoxide, carbonic acid Sodium, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, etc., as well as one or a mixture of two or more thereof.
  • the coupling reaction can be carried out in an organic solvent, wherein the organic solvent can be selected from: diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, ethylene glycol ethyl ether, ethylene glycol diethyl ether, ethylene glycol Ether solvents such as methyl ether, diglyme, or anisole, aromatic hydrocarbon agents such as benzene, toluene, and xylene, chlorobenzene, dichlorobenzene, N,N-dimethylformamide, N,N- One type or a mixture of two or more types of dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, sulfolane, etc. can be used.
  • the organic solvent can be selected from: diethyl ether, tetrahydrofuran, 2-methyltetrahydrofuran, 1,4-dioxane, ethylene glycol
  • the present invention also provides an organic electroluminescent material, the raw material of which includes the above-mentioned azaadamantane compound; the organic electroluminescent material including the azaadamantane compound of the present invention has the ability of carrier transport.
  • the organic electroluminescent material is a hole injection layer material, a hole transport layer material, a hole blocking layer material, a light emitting layer material, an electron transport layer material, an electron injection layer material, a capping layer (referred to as a CPL layer) ) material or electron blocking layer material.
  • the present invention also provides the application of the above-mentioned azaadamantane compound in preparing organic electroluminescent elements.
  • the present invention also provides an organic electroluminescent element, which includes: a first electrode, a second electrode, a CPL layer, and one or more organic layers placed between the first electrode and the second electrode; At least one of the organic layer and the CPL layer includes the above-mentioned azaadamantane compound.
  • the organic electroluminescent element includes a cathode, an anode, CPL and at least one light-emitting layer. In addition to these layers, it may contain 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, excitation layers, etc. sub-blocking layer, electron blocking layer and/or charge generating layer. An intermediate layer having, for example, an exciton blocking function can also be introduced between the two luminescent layers. However, it should be noted that each of these layers does not necessarily have to be present.
  • the organic electroluminescent element described here may include one light-emitting layer, or it may include a plurality of light-emitting layers.
  • a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer.
  • Particularly preferred are systems with three luminescent layers, wherein the three layers can exhibit blue, green and red luminescence. If more than one luminescent layer is present, according to the invention at least one of these layers contains a compound of the invention.
  • the organic electroluminescent element according to the present invention does not include a separate hole injection layer and/or hole transport layer and/or hole blocking layer and/or electron transport layer, that is, the light emitting layer and the hole injection layer or The anode is directly adjacent, and/or the light-emitting layer is directly adjacent to the electron transport layer or electron injection layer or the cathode.
  • OLEDs comprise at least one organic layer disposed between and electrically connected to an anode and a cathode.
  • FIG. 1 shows a schematic diagram of an organic light-emitting device 100. Illustrations are not necessarily 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, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL). )110.
  • Device 100 may be fabricated by sequentially depositing the described layers.
  • FIG. 2 shows a schematic diagram of an organic light-emitting device 200 including 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 light-emitting layer 205, an electron transport layer 206, a charge generation layer 207, a hole injection layer 208, and a hole transport layer 209 , the second light-emitting layer 210, the electron transport layer 211, the electron injection layer 212 and the cathode 213.
  • Device 200 may be prepared by sequentially depositing the described layers.
  • the device 200 has two light-emitting layers of the same light color.
  • materials similar to those described with respect to device 100 may be used.
  • Figure 2 provides an example of how some layers may be added from the structure of device 100.
  • hole transport layer 204 transports holes and injects holes into light emitting layer 205, and may be described as a hole transport layer or an electron blocking layer.
  • an OLED may be described as having an organic layer disposed between a cathode and an anode. This organic layer may comprise a single layer or may further comprise multiple layers of different organic materials as described for example in Figures 1 and 2.
  • OLEDs containing polymeric materials may also be used, such as PLEDs containing polymeric materials.
  • an OLED with a single organic layer or multiple stacks may be used.
  • OLED structures can depart from the simple layered structure illustrated in Figures 1 and 2.
  • the substrate may include angled reflective surfaces to improve light coupling.
  • the organic electroluminescent element of the present invention in addition to one or more of the above-mentioned organic layers containing the above-described indene derivative, the organic layer and the electrode can be formed using materials and methods known in the art. manufacture.
  • the substance that can be used as an anode included in the organic electroluminescent element according to the present invention is not particularly limited.
  • metals such as vanadium, chromium, copper, zinc, gold, aluminum, or alloys thereof can be used. ;
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; polythiophene, poly(3-methyl) Conductive polymers such as thiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole and polyaniline; and carbon black, etc.
  • the material that can be used as the cathode included in the organic electroluminescent element according to the present invention is not particularly limited.
  • magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum can be used.
  • silver, tin or lead and other metals or their alloys; and multi-layer structure materials such as LiF/Al or Li 2 O/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.
  • silicon wafers, quartz, glass plates, metal plates or plastic films and sheets can be used.
  • organic electroluminescent components are preferred in which one or more layers can be applied by means of a sublimation method, wherein the layers are deposited by vapor deposition in a vacuum sublimation device at an initial pressure of less than 10 -5 Pa, preferably less than 10 -6 Pa. to apply the material.
  • the initial pressure may also be even lower, for example below 10 -7 Pa.
  • organic electroluminescent components in which one or more layers can also be applied by means of an organic vapor deposition method 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, in which the material is applied directly through a nozzle and is therefore structured.
  • organic electroluminescent elements produced from solution, for example by spin coating, or by means of any desired printing method, such as screen printing, flexographic printing, lithography, photothermography, thermal transfer printing, spray printing, etc. Ink printing or nozzle printing to produce one or more layers.
  • Soluble compounds can be obtained, for example, by appropriately substituting compounds represented by formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers.
  • hybrid methods are possible, in which one or more layers are applied, for example, from solution and one or more further layers are applied by vapor deposition.
  • the invention therefore also relates to a method for producing an organic electroluminescent element according to the invention, comprising applying at least one layer by means of a sublimation method and/or applying at least one layer by means of an organic vapor deposition method or by means of carrier gas sublimation , and/or at least one layer is applied from solution by spin coating or by means of printing methods.
  • the present invention relates to compounds comprising at least one compound of the invention indicated above.
  • the compounds may preferably also comprise other compounds.
  • Processing the compounds of the invention from the liquid phase requires processing of formulations of the compounds of the invention, which may be, for example, solutions, dispersions or emulsions.
  • formulations of the compounds of the invention which may be, for example, solutions, dispersions or emulsions.
  • mixtures of two or more solvents may preferably be used.
  • 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, especially 3-phenoxytoluene, (-)-fenone, 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, ⁇ -terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohe
  • 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, a CPL layer or an electron blocking layer.
  • the raw materials used in the present invention can be purchased from commercial stores. Any range recorded in the present invention includes the end value and any value between the end value and the end value or any value between the end value. Any subrange formed by.
  • the invention also relates to mixtures comprising at least one compound of formula (I) or the preferred embodiments described above and at least one further compound. If the compounds according to the invention are used as matrix materials, the other compounds can be fluorescent or phosphorescent emitters. The mixture may then additionally contain other materials as additional matrix materials.
  • the invention also relates to the use of the compounds of the invention in electronic components. Preferably, as mentioned above and below, the compounds according to the invention are used in the hole transport layer or as matrix material in the emissive layer.
  • the compounds according to the invention and the electronic components obtainable therefrom, in particular organic electroluminescent components differ from the prior art by one or more of the following surprising advantages:
  • the electronic components obtainable using the compounds of the present invention exhibit high efficiency, especially high luminous efficiency and high external quantum efficiency.
  • the compounds of the present invention provide low operating voltage.
  • the compounds according to the invention can be processed using conventional methods, so that cost advantages can also be achieved.
  • the films obtainable using the compounds of the present invention exhibit excellent qualities, especially in terms of film uniformity.
  • the compounds of the invention can be produced in a very fast and easy manner using conventional methods, so that cost advantages can also be achieved.
  • FIG. 1 shows a schematic diagram of an organic light-emitting device 100. Illustrations are not necessarily 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, an electron transport layer 107, an electron injection layer 108, a cathode 109, and a capping layer (CPL). )110.
  • Device 100 may be fabricated by sequentially depositing the described layers.
  • 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, hole injection 203, hole transport layer 204, first light-emitting layer 205, electron transport layer 206, charge generation layer 207, hole injection layer 208, hole transport layer 209, The second light-emitting layer 210, the electron transport layer 211, the electron injection layer 212 and the cathode 213.
  • Device 200 may be prepared by sequentially depositing the described layers.
  • the luminescence peak shapes of the first luminescent layer and the second luminescent layer may be overlapping or cross-overlapping or non-overlapping.
  • materials similar to those described with respect to device 100 may be used.
  • Figure 2 provides an example of how some layers may be added from the structure of device 100.
  • test instruments and methods for performance testing of OLED materials and components in the following examples are as follows:
  • Luminance and chromaticity coordinates tested using spectral scanner PhotoResearch PR-715;
  • the preparation method of compound D275 includes the following steps:
  • Int-1 12.0mmol of Int-1 was dissolved in 60mL of xylene, and under nitrogen protection, 10.0mmol of N-biphenyl-4'-(9-carbazolyl)-biphenyl-4-amine and 15.0mmol of Sodium tert-butoxide, 0.1 mmol copper iodide, 0.1 mmol Pd 2 (dba) 3 catalyst, then add 0.2 mmol Xantphos, raise the temperature to 110°C and stir for 16 hours, then cool to room temperature, add 20 mL of water to dilute, Extract with toluene, collect the organic phase, dry, filter, and concentrate the filtrate to dryness under reduced pressure.
  • *—T 3 —* is selected from *—O—*, *—S—* or one of the following structures:
  • *—T 3 —* is selected from *—O—*, *—S—* or one of the following structures:
  • *—T 3 —* is selected from *—O—*, *—S—* or one of the following structures:
  • the preparation method of compound D483 includes the following steps:
  • *—T 3 —* is selected from *—O—*, *—S—* or one of the following structures:
  • An organic electroluminescent element 100 has a structure as shown in Figure 1, including a substrate 101, an anode layer 102 provided on the substrate 101, a hole injection layer 103 provided on the anode layer 102, and a hole injection layer 103 provided on the anode layer 102.
  • the preparation method of the cathode layer 109 and the CPL layer 110 disposed on the cathode layer 109 includes the following steps:
  • Example 6 Following the same steps as in Example 6, replace RH12 in step 5) with the compound represented by formula (I) of the present invention, and obtain the OLED component of the present invention.
  • the performance test comparison results of the component are shown in Table 8.
  • a digital source meter and a luminance meter were used to measure the driving voltage and current efficiency of the organic electroluminescent elements prepared in Examples 6 to 10, as well as the lifetime of the elements. Specifically, increase the voltage at a rate of 0.1V per second, measure the voltage when the current density of the organic electroluminescent element reaches 10mA/ cm2 , which is the driving voltage, and measure the brightness at this time; the ratio of brightness to current density That is the current efficiency; the LT95% life test is as follows: use a luminance meter to maintain a constant current at a brightness of 1000cd/ m2 , and measure the time for the brightness of the organic electroluminescent element to decay to 950cd/ m2 , in hours, all data All are normalized results of comparison components.
  • the light-emitting element prepared by using the azaadamantane compound of the present invention as a hole transport layer material also has a reduced driving voltage, a significant improvement in luminous efficiency, and a LT95% lifespan under the condition of a current density of 10 mA/cm 2 It has obvious advantages and is a hole transport layer material with good performance.
  • azaadamantane contains nitrogen atoms of lone electron pairs, which has less impact on molecular film formation. Compared with adamantane, the hole mobility is increased, so its hole mobility is improved. It is superior to the comparative compound HT08 in terms of molecular film formation and carrier transport properties, and has more advantages in component performance and lifespan.
  • the light-emitting element prepared by using the azaadamantane compound of the present invention as an electron blocking layer material also has a lower driving voltage and a significantly improved luminous efficiency under the condition of a current density of 10 mA/ cm2 , and the LT95% lifespan has a great The amplitude is improved and it is an electronic material with excellent performance.
  • azaadamantane contains nitrogen atoms with lone electron pairs, which is more conducive to transporting holes and blocking electrons, reducing the probability of exciton formation in the non-emitting layer. Therefore, its performance in light-emitting components is even better.
  • the light-emitting element prepared by using the azaadamantane compound of the present invention as the host material of the light-emitting layer also has a reduced driving voltage and a significant improvement in luminous efficiency under the condition of a current density of 10 mA/ cm2 , and the LT95% life span is It has been greatly improved and is a light-emitting layer material with excellent performance.
  • the difference is that the steric hindrance of dimethyl fluorene is small.
  • Replacing the dimethyl group with azaadamantane not only increases the steric hindrance, but also helps to block the transport of holes. Therefore, the molecules constitute D-A bipolarity, and the carrier transmission in the light-emitting layer is more balanced, which is more conducive to the formation of excitons in the light-emitting layer, so its performance in light-emitting elements is better.
  • Me is methyl; Ph is phenyl; PhPh is biphenyl; Nap is naphthyl; FR is fluorenyl.
  • the light-emitting element prepared by using the azaadamantane compound of the present invention as an electron transport layer material also has a lower driving voltage and a significantly improved luminous efficiency under the condition of a current density of 10 mA/ cm2 , and the LT95% lifespan has a great The amplitude is improved and it is an electronic material with excellent performance.
  • azaadamantane contains nitrogen atoms with lone electron pairs.
  • the introduction of nitrogen atoms enhances the three-dimensional rigidity of adamantane, which is more conducive to the transmission of electrons and excitons. formed, so it performs better in light-emitting components.

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Abstract

La présente invention concerne le domaine technique des matériaux électroluminescents organiques, en particulier un composé d'aza-adamantane et un élément électroluminescent organique. La formule structurale du composé d'aza-adamantane est telle que représentée dans la formule (I). Le composé d'aza-adamantane tel que représenté dans la formule (I) selon la présente invention est appliqué à un élément électroluminescent organique, la tension d'attaque pouvant ainsi être significativement réduite, et l'efficacité lumineuse et la durée de vie pouvan ainsi être améliorées.
PCT/CN2023/099910 2022-06-16 2023-06-13 Composé d'aza-adamantane et élément électroluminescent organique WO2023241569A1 (fr)

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