WO2024012469A1 - Dérivé de carbazole et son utilisation dans un élément électroluminescent organique - Google Patents

Dérivé de carbazole et son utilisation dans un élément électroluminescent organique Download PDF

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WO2024012469A1
WO2024012469A1 PCT/CN2023/106867 CN2023106867W WO2024012469A1 WO 2024012469 A1 WO2024012469 A1 WO 2024012469A1 CN 2023106867 W CN2023106867 W CN 2023106867W WO 2024012469 A1 WO2024012469 A1 WO 2024012469A1
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substituted
unsubstituted
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aryl
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曹建华
谢佩
杨美跃
李留洋
郭文龙
李程辉
王振宇
唐伟
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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 a carbazole derivative and its application in organic light-emitting elements.
  • organic luminescence refers to the phenomenon of emitting light when electrical energy is applied to organic substances. 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, and electrons will be injected from the cathode to the organic layer. When the injected holes and electrons meet , an exciton is formed, which emits light and heat when it transitions to the ground state.
  • organic electroluminescent display technology has matured, and some products have entered the market.
  • problems that need to be solved during the industrialization process.
  • various organic materials used to make components including their carrier injection and transmission properties, material electroluminescence properties, service life, color purity, matching between various materials and between various electrodes, etc.
  • the problem has not yet been solved; in particular, the luminous efficiency and service life of light-emitting components have not yet met practical requirements, which has greatly restricted the development of organic light-emitting diode (OLED) technology.
  • Metal complex phosphorescent materials that utilize triplet luminescence have high luminous efficiency, and their green and red light materials have met the requirements for use.
  • metal complex phosphorescent materials require phosphorescent materials or hole materials with high triplet energy levels and match. Therefore, the development of phosphorescent materials or hole materials with high triplet energy levels is an urgent need for the current development of OLEDs.
  • substituted or unsubstituted means: selected from hydrogen, deuterium, halogen atom, hydroxyl, nitrile group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group or Its carboxylate, 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 group, 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
  • the 2 -C 60 heterocyclic aryl group may be substituted or unsubstituted by one or more substituents
  • the solution of the present invention is to provide a carbazole derivative, which can improve the thermal stability of the material and the ability to transport carriers.
  • the organic electroluminescent element prepared by using the compound can significantly reduce the driving voltage, Improve luminous efficiency and lifespan.
  • 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;
  • X 1 , X 2 and X 3 are each independently N or CR 7 ;
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are selected from hydrogen, deuterium, fluorine, hydroxyl, nitrile group, nitro group, carboxyl group or its carboxylate or sulfonic acid group.
  • n an integer from 0 to 5;
  • Ar 1 is selected from the group consisting of a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 fused ring aryl group, or a substituted or unsubstituted C 2 -C 60 heterocyclic aryl group. Group.
  • X 1 , X 2 and X 3 are each independently CR 7 ;
  • n 0, 1 or 2;
  • the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are each independently selected from hydrogen, deuterium, fluorine, nitrile, phenyl, diphenyl, terphenyl, and naphthyl. , a group consisting of phenanthrenyl, triphenylene, carbazole, dibenzofuran or dibenzothiophene;
  • the Ar 1 is a group selected from the following materials: 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, dibenzofuran, thiophene, benzothiophen
  • the Ar 1 is selected from the group consisting of the following groups II-1 to II-17:
  • Z 1 and Z 2 are each independently selected from hydrogen, deuterium, halogen, hydroxyl, nitrile group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxyl group or its carboxylate, sulfonic acid group or its sulfonate , phosphate group or its phosphate, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 1 -C 40 alkoxy group, C 3 -C 40 cycloalkyl group, C 3 -C 40 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 -
  • T 1 means O, S, CR'R" or NAr';
  • R', R" are each independently selected from hydrogen, deuterium, C 1 to C 40 alkyl group, C 1 to C 40 heteroalkyl group, substituted or unsubstituted C 6 to 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 multiple substituted Or an unsubstituted ring, containing or not containing one or more heteroatoms N, P, B, O or S in the formed ring; more preferably, R', R" is methyl, phenyl or fluorenyl ;
  • Ar' is selected from C 1 to C 40 alkyl, C 1 to C 40 heteroalkyl, C 3 to C 40 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; more preferably, Ar ' is methyl, ethyl, phenyl, biphenyl or naphthyl.
  • the L 1 is selected from the group consisting of the following groups III-1 to III-15:
  • Z 11 and Z 12 are each independently selected from hydrogen, deuterated hydrogen, 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 sulfonate Acid salt, phosphate group or its phosphate, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 1 -C 40 alkoxy group, C 3 -C 40 cycloalkane group, C 3 -C 40 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 An ether group, or a group consisting of substituted or unsubsti
  • 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 3 means O or S.
  • the carbazole derivative is selected from compounds represented by the following formula C470-C625:
  • *—G—* is selected from *—O—*, *—S—* or one of the following structures:
  • the present invention further provides a method for preparing the carbazole derivative, as shown in Scheme 1:
  • the raw materials for synthesizing the carbazole derivatives represented by formula (I) can be purchased commercially.
  • the principle, operation process, conventional post-treatment, column purification, recrystallization purification and other means of this method are well known to synthetic practitioners in the field. , the synthesis process can be completely realized, and the target product can be obtained in both theory and practice.
  • the carbazole derivative of formula (I) is a substitution reaction between 3-R 1 -substituted-5-halogenated carbazole I-0 and R 2 -yl acetylene to prepare intermediate I-1;
  • Intermediate I -1 undergoes ring closing reaction to prepare intermediate I-2;
  • carbazole intermediate I-2 undergoes halogenation reaction to obtain I-3;
  • polyhalogenated intermediate I-3 undergoes coupling reaction with carbazole or carboline to prepare the present invention
  • Compound I-4 and Ar 1 -(L 1 )nY 4 undergo a coupling reaction to prepare compound formula (I).
  • the intermediate Ar 1 -(L 1 )nY 4 can be 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 A mixture of more than one 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 Any one of sodium, potassium carbonate, cesium carbonate, lithium, potassium hydride, triethylamine, cesium fluoride, etc., or a mixture of two or more.
  • 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 contains the carbazole derivative; and the organic electroluminescent material containing the compound of the present invention has the ability of carrier transport.
  • the invention also provides an application of organic electroluminescent material in preparing organic electroluminescent elements.
  • the present invention also provides an organic electroluminescent element, which includes: a first electrode, a second electrode, a capping layer and one or more organic layers placed between the first electrode and the second electrode;
  • the material of at least one of the organic layer or the capping layer includes the above-mentioned carbazole derivative.
  • the organic electroluminescent element includes a cathode, an anode and at least one light-emitting layer. In addition to these layers, it may contain other layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers, electron blocking layers layer and/or charge generation 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 device described herein may include one light emitting layer, or it may include multiple light emitting layers. That is, 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 carbazole derivative according to 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 electron blocking layer or hole transport layer
  • the hole transport 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.
  • organic electroluminescent components are preferred in which one or more layers are applied by means of a sublimation method, wherein the layer is 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. Apply the material.
  • the initial pressure may also be even lower, for example below 10 -7 Pa.
  • 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, 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, applying at least one layer by means of a sublimation method, and/or characterized in that at least one layer is applied by means of an organic vapor deposition method or by means of carrier gas sublimation. layers, and/or is characterized in that at least one layer is applied by spin coating from solution or by means of printing methods.
  • the invention relates to carbazole derivatives comprising at least one of the invention indicated above.
  • the compounds may preferably also comprise other compounds.
  • Processing the compounds according to the invention from the liquid phase, for example by spin coating or by printing methods, requires formulation of the compounds according to the invention.
  • These formulations 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 or an electron blocking layer.
  • the present invention also provides a consumer product, which includes the above-mentioned organic electroluminescent element.
  • 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 carbazole derivative (shown in formula (I)) of the present invention has a high triplet energy level, increases the conjugation of the carbazole mother core, improves the thermal stability of the material and the ability to transport carriers,
  • the application of the carbazole derivative in organic electroluminescent elements can significantly reduce the driving voltage and improve the luminous efficiency and lifespan.
  • FIG. 1 shows a schematic diagram of an organic light-emitting device 100. Illustrations are not necessarily to scale.
  • Device 100 may include substrate 101, anode 102, hole injection layer 103, hole transport layer 104, electron blocking layer 105, light emitting layer 106, hole blocking layer 107, electron transport layer 108, electron injection layer 109, cathode 110 and capping layer (CPL) 111.
  • 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 C483 includes the following steps:
  • Compound B-1 is prepared by referring to the above-mentioned similar synthetic method, only replacing the trimethylsilyl acetylene in the first step with an acetylene substituted by an aryl acetylene or an alkyl acetylene, for example, phenyl acetylene.
  • Compound B-2 was prepared by referring to the above-mentioned similar synthesis method, only replacing trimethylsilyl acetylene in the first step with 3-pyridine acetylene.
  • the preparation method of compound C523 includes the following steps:
  • the preparation method of compound C577, taking G as O as an example, includes the following steps:
  • intermediate Int-5 (reactant 1) was dissolved in 40 mL of THF and 10 mL of triethylamine, 0.2 g of 10% palladium/carbon was added, hydrogen was introduced to 0.1 MPa, and the reaction was stirred at room temperature for 12 hours. Filter, wash the filter cake with THF, concentrate the filtrate to dryness under reduced pressure, separate and purify with a silica gel column, and then recrystallize with toluene/THF to obtain compound Int-9 with a yield of 100%.
  • *—G—* is selected from *—O—*, *—S—* or one of the following structures:
  • the OLED element of this embodiment is a top-emitting light-emitting element, including a substrate 101, an anode layer 102 provided on the substrate 101, a hole injection layer 103 provided on the anode layer 102, The hole transport layer 104 provided on the hole injection layer 103, the electron blocking layer 105 provided on the hole transport layer 104, the organic light emitting layer 106 provided on the electron blocking layer 105, the organic light emitting layer 106 provided on the organic light emitting layer 106.
  • the preparation method of the OLED element includes follow these steps:
  • An organic electroluminescent element 200 has a structure as shown in Figure 2, which includes a substrate 201, 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, second light emitting layer 210, electron transport layer 211, electron injection layer 212 and cathode 213.
  • a digital source meter and a luminance meter were used to measure the driving voltage and current efficiency of the organic electroluminescent element prepared in Example 4 and Comparative Examples 1 and 2, as well as the lifetime of the element. Specifically, increase the voltage at a rate of 0.1V per second, measure the voltage when the brightness of the organic electroluminescent element reaches 1000cd/ m2 , which is the driving voltage, and measure the current density at this time; the ratio of brightness to current density That is the current efficiency; the LT90% 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 900cd/ m2 , in hours.
  • the data listed in Table 4 are relative data compared to Comparative Element 1.
  • Ph is a phenyl group
  • PhPh is a biphenyl group
  • Me is a methyl group
  • FR is a 9,9-fluorenyl group.
  • the difference between compound HS01 in Comparative Example 1 is that benzocarbazole has weak planar conjugation ability, unbalanced transmission of holes and electrons, and its ability to accept holes is stronger than its ability to accept electrons.
  • This imbalance in transmission affects the formation of excitons in the light-emitting layer, resulting in high voltage, low efficiency, and reduced lifetime.
  • the compound of the present invention introduces bonded carbazole on the basis of benzocarbazole, which improves the conjugation ability of the mother core, so it has excellent performance in molecular film formation and charge transmission, and the charge transmission within the element More balanced and improved component performance.
  • the difference is that HS02 is a naphthocarbazole.
  • the planar conjugation ability is enhanced, the planar conjugation ability is weak compared with the carbazole compound of the present invention.
  • the incorporation of the carbazole ring forms a large conjugated fused ring structure, so its performance is excellent in molecular film formation and charge transmission.
  • the charge transmission within the component is more balanced.
  • the component performance, especially the LT90% lifespan, is greatly improved. Higher than the comparison element, therefore the carbazole derivative of the present invention is an organic electroluminescent material with excellent performance.

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Abstract

La présente invention concerne un dérivé de carbazole et son utilisation dans un élément électroluminescent organique. Le dérivé de carbazole a une structure de carbazole fusionnée, un niveau d'énergie d'état de triplet élevé est obtenu, et la conjugaison d'un noyau parent de carbazole est améliorée, ce qui permet d'améliorer la stabilité thermique d'un matériau et la capacité de transport des véhicules. Le dérivé de carbazole peut être utilisé dans un élément électroluminescent organique ce qui permet de réduire de manière significative la tension de commande, d'améliorer l'efficacité d'émission de lumière et de prolonger la durée de vie. La formule développée du dérivé de carbazole est représentée par la formule (I).
PCT/CN2023/106867 2022-07-14 2023-07-12 Dérivé de carbazole et son utilisation dans un élément électroluminescent organique WO2024012469A1 (fr)

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