WO2022242521A1 - Composé azacyclique condensé, son utilisation, et dispositif électroluminescent organique comprenant un composé azacyclique condensé - Google Patents

Composé azacyclique condensé, son utilisation, et dispositif électroluminescent organique comprenant un composé azacyclique condensé Download PDF

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WO2022242521A1
WO2022242521A1 PCT/CN2022/092188 CN2022092188W WO2022242521A1 WO 2022242521 A1 WO2022242521 A1 WO 2022242521A1 CN 2022092188 W CN2022092188 W CN 2022092188W WO 2022242521 A1 WO2022242521 A1 WO 2022242521A1
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朱运会
王彦杰
张其胜
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Zhejiang Hongwu Technology Co Ltd
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    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
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    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the invention relates to the technical field of organic electroluminescence, in particular to a novel organic compound and its application, and an organic electroluminescent device containing the compound.
  • OLED Organic Light Emitting Devices
  • OLED Organic Light Emitting Devices
  • OLED Organic Light Emitting Devices
  • the holes generated by the anode and the electrons generated by the cathode will move, inject into the hole transport layer and the electron transport layer respectively, and migrate to the light-emitting layer.
  • a Energy excitons which excite light-emitting molecules and eventually produce visible light.
  • OLED has the characteristics of self-illumination, wide viewing angle, wide color gamut, short response time, high luminous efficiency, low operating voltage, low cost, and simple production process. It can be made into large-size and/or flexible ultra-thin panels, which is a development
  • the new display technology with high speed and high process integration has been widely used in display products such as TVs, smart phones, tablet computers, vehicle displays, lighting, etc., and will be further applied in creative display products such as large-size displays and flexible screens .
  • Organic optoelectronic materials applied to OLED devices can be divided into light-emitting layer materials and auxiliary functional layer materials in terms of use.
  • the light-emitting material layer materials include guest materials (also called light-emitting materials, doping materials) and host materials (also called According to different luminescent mechanisms, luminescent materials are divided into fluorescent materials, phosphorescent materials and thermally activated delayed fluorescent materials, and auxiliary functional layer materials are divided into electron injection materials and electron transport materials according to the different properties of electron or hole transport speeds. , Hole blocking materials, electron blocking materials, hole transport materials, hole injection materials.
  • the most studied and most important is the improvement of the performance of the light-emitting devices of the three primary colors of red, green, and blue.
  • the light-emitting dopant used in the light-emitting layer has a decisive impact on the color, efficiency, stability and other properties of the electroluminescent device.
  • light-emitting dopant materials with high efficiency and narrow emission are still in short supply.
  • the current blue light-emitting doped materials have problems such as low efficiency, short lifespan and insufficient color purity, such as patent (CN200310124405.8, application date December 24, 2003) and literature (ACS Appl.Mater.Interfaces 2018, 10,30022-30028) in the pyrene compound, the pyrene molecule has a planar rigid ⁇ -conjugated structure, which is easy to achieve high luminous efficiency, and is a blue light-emitting dopant structure with excellent performance.
  • its molecular structure is prone to intermolecular aggregation, resulting in reduced efficiency and lifetime; on the other hand, its emission spectrum presents a strong shoulder emission, resulting in a wide half-width of the spectrum and low color purity.
  • the present invention provides a novel fused nitrogen heterocyclic organic compound, which is composed of formula (1) and formula (2):
  • Z 1 to Z 14 are independently represented as CR 1 to CR 14 or N; in formula (2), when the L bond is connected to Z 1 to Z 14 , then Z 1 to Z 14 are represented as C ;
  • the substituent group represented by formula (2) when the substituent group represented by formula (2) is substituted by formula (1), it is only substituted at Z 1 , Z 2 , Z 5 , Z 6 , Z 8 , Z 9 , Z 12 or Z 13 ;
  • L is independently selected from single bonds, substituted or unsubstituted linear or branched alkylene groups with 1 to 20 carbon atoms, substituted or unsubstituted ring-forming carbon atoms with 3 to 20 Cycloalkylene, substituted or unsubstituted arylene with 6 to 30 ring carbon atoms, substituted or unsubstituted heteroarylene with 2 to 30 ring carbon atoms, substituted or unsubstituted Subfused aryl rings with 10 to 50 ring carbon atoms, substituted or unsubstituted subfused heterocyclic rings with 6 to 50 ring atoms;
  • L is independently selected from the substituted or unsubstituted following groups, but not limited to the following groups:
  • R 1 to R 14 substituent groups are independently selected from hydrogen atom, deuterium atom, halogen atom, cyano group, nitro group, substituted silicon group, substituted or unsubstituted carbon atoms with 1 to 50 Alkyl, substituted or unsubstituted alkenyl with 1 to 20 carbons, substituted or unsubstituted alkynyl with 1 to 20 carbons, substituted or unsubstituted alkoxy with 1 to 50 carbons, substituted or unsubstituted Substituted fluoroalkyl with 1 to 20 carbons, substituted or unsubstituted fluoroalkoxy with 1 to 20 carbons, substituted or unsubstituted cycloalkyl with 3 to 50 ring carbon atoms, substituted or An unsubstituted aryl group with 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group with 5 to 50 ring atoms;
  • the substituent groups R 15 to R 16 are independently selected from substituted or unsubstituted alkyl groups with 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl groups with 3 to 50 ring carbon atoms , a substituted or unsubstituted aryl group with 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group with 5 to 50 ring atoms;
  • the substituent groups R 1 to R 16 can bond with each other to form a substituted or unsubstituted saturated or unsaturated ring, and can also form a substituted or unsubstituted saturated or unsaturated ring with an adjacent aromatic ring or heteroaryl ring. the fused ring;
  • R 1 to R 16 substituent groups are independently selected from any one or more of the following groups:
  • substituted in “substituted or unsubstituted” in the above compounds means that the substituents are independently selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, hydroxyl groups, monovalent alkyl groups with 1 to 10 carbon atoms Or a cycloalkyl group, a monovalent monocyclic aryl group or a fused ring aryl group with 6 to 30 carbon atoms, a monovalent heterocyclic group or a condensed ring heteroaryl group with a carbon number of 2 to 50;
  • the "substituted" group in “substituted or unsubstituted” is independently any one or more selected from the following groups:
  • formula (1) and formula (2) protected by the present invention can preferably select the following specific structural compounds Compound 1 ⁇ Chem 216, and these compounds are only representative:
  • the second object of the present invention is to provide an organic electroluminescent device.
  • the organic electroluminescent device comprises an anode, a cathode and at least one layer of organic thin film between the anode and the cathode, and the organic thin film contains one or more organic electroluminescence compounds composed of formula (1) and formula (2).
  • Luminescent compound Luminescent compound.
  • the organic layer includes a light-emitting layer and a functional layer, and the compound formed by the combination of formula (1) and formula (2) can be used alone or in combination as a hole injection layer, a hole transport layer or a light-emitting material.
  • the third object of the present invention is to provide an organic electroluminescent device.
  • an organic electroluminescent device with high color purity and low driving voltage, high efficiency and long life is obtained by optimizing the structure of the device.
  • the fused nitrogen heterocyclic compound protected by the present invention is a kind of amino-substituted bis-indolophenazine compound.
  • This kind of material has a planar conjugated rigid structure, can inhibit the twisting of the structural unit in the excited state, and has a narrow emission spectrum, and has high luminous efficiency; the combination of the arylamine unit of formula (2) and the structure of formula (1) can adjust the energy level and band gap of the molecule to obtain fluorescence of a suitable wavelength, and at the same time, the steric hindrance of the arylamine unit, It is beneficial to inhibit the aggregation between material molecules and significantly improve the device performance.
  • Fig. 1 is a schematic diagram of the structure of an organic electroluminescent device applied by the compound of the present invention, wherein, the meanings of each layer structure of the device are as follows:
  • Transparent substrate layer 2. ITO anode layer, 3. Hole injection layer, 4. Hole transport layer A, 5. Hole transport layer B (or electron blocking layer), 6. Light emitting layer, 7. Electron transport Layer B (or hole blocking layer), 8, electron transport layer A, 9, electron injection layer, 10, cathode reflective electrode layer.
  • Figure 2 is the fluorescence spectrum of Comparative Compound-1 in toluene solution at room temperature [25°C, 300K].
  • Figure 3 is the fluorescence spectrum of Comparative Compound-2 in toluene solution at room temperature [25°C, 300K].
  • Figure 4 shows the fluorescence spectrum of CH66 in toluene solution at room temperature [25°C, 300K].
  • the reaction was stopped, cooled to room temperature, extracted three times with ethyl acetate/water, dried over anhydrous sodium sulfate, concentrated by rotary evaporation, and separated on a silica gel column to obtain 5.48 g of the target product with a yield of 89%.
  • the organic electroluminescence device described in the solution of the present invention comprises an anode layer, a cathode layer and at least one organic layer between the anode and the cathode.
  • the organic layer is a film layer formed by laminating multiple layers of organic compounds.
  • the organic layer may also contain inorganic compounds.
  • At least one of the organic layers of the organic electroluminescent device described in the solution of the present invention is a light-emitting layer.
  • the organic layer may also include other functional layers, for example, there may be one or more hole injection layers, hole transport layers, or electron blocking layers between the anode layer and the light-emitting layer, and between the two light-emitting layers It is also feasible to have an exciton blocking layer or an intermediate layer with similar functions, and one or more hole blocking layers, electron transport layers, or electron injection layers exist between the light emitting layer and the cathode layer. It should be noted that these functional layers do not necessarily exist.
  • the organic electroluminescent device of the present invention can be a fluorescent or phosphorescent device, or a fluorescent and phosphorescent hybrid device; it can be a single light-emitting device, or a series device with a plurality of light-emitting units; in addition, it can be It is a single-color light-emitting device, or a mixed-color device, or a white light-emitting device.
  • the light emitting layer may contain multiple guest materials and multiple host materials.
  • the guest material may be a fluorescent material, a phosphorescent material and/or a thermally activated delayed fluorescent material.
  • the host material refers to the host material that occupies most of the components in the light-emitting layer.
  • the host material that is doped and combined with fluorescent materials is called “fluorescent host”, and the host material that is doped and combined with phosphorescent materials is called “phosphorescent host”. ". It should be noted that the selection of the host material does not depend on its molecular structure, but on the basis of the host material as the guest material.
  • the compounds of the invention according to the above embodiments can be used in different organic layers. Preference is given to organic electroluminescent devices in which the compounds according to the invention are used as hole-injection material, hole-transport material or emitting material of the emitting layer.
  • the use of the compounds according to the invention according to the above embodiments is likewise suitable for use in organic electronic devices.
  • the compounds according to the invention are used as light-emitting materials for the light-emitting layer in organic electroluminescent devices.
  • Device Examples 1-8 Manufacture of an organic electroluminescent device used as a blue light-emitting material for the light-emitting layer
  • ITO indium tin oxide
  • anode an indium tin oxide transparent electrode
  • UV ultraviolet-ozone cleaning
  • the film thickness of ITO was 130 nm.
  • HIL hole injection layer
  • a hole transport layer A (HTL) was vapor-deposited on the hole injection layer to have a film thickness of 60 nm.
  • an electron blocking layer (EBL) was vapor-deposited on the hole transport layer A to have a film thickness of 5 nm.
  • a light-emitting layer (EML) was co-deposited on the electron blocking layer with a film thickness of 20 nm.
  • the light-emitting layer (EML) adopts multi-source co-evaporation to evaporate the light-emitting material BD and the host material BH of the light-emitting layer, wherein the doping concentration of the light-emitting material is 2% by weight.
  • HBL hole blocking layer
  • ETL electron transport material
  • Liq 8-hydroxyquinolate lithium
  • Example 1 The structure of the organic electroluminescent device in Example 1 is shown in Figure 1, and Figure 1 also shows the stacking sequence and function of each functional layer.
  • the molecular structures of the materials used in OLEDs are shown in Table 1.
  • the device structure of the device embodiment 1 is specifically: ITO (130)/HATCN (15)/HTL (60)/EBL (5)/BH:2 (20, weight 2%)/HBL (5)/ETL: Liq(30, 50% by weight)/Liq(1)/Al(100), it should be noted that the numbers in parentheses represent the film thickness (unit: nm).
  • Device Example 2-Device Example 8 The difference between Device Example 2-Device Example 8 and Device Example 1 is that the Compound 2 of the present invention used in the light-emitting layer is replaced by other compounds of the present invention, see Table 2 for details.
  • Comparative Examples 1-2 differ in that the luminescent material in the organic electroluminescent device is changed to Comparative Compound-1-Comparative Compound-2, and the device performance test data obtained are shown in Table 2.
  • the OLEDs were characterized by standard methods. For this purpose, the electroluminescence spectrum, current efficiency (measured in cd/A), power efficiency (measured in lm/W) and external quantum efficiency (EQE, measured in %) were determined as a function of luminous density from the Calculation of current/voltage/luminous density characteristic lines (IUL characteristic lines) of primary emission characteristics. Determine the required voltage V10 at a current density of 10 mA/ cm2 .
  • EQE represents the external quantum efficiency at a current density of 10mA/ cm2
  • T95 represents the working time of the device when the brightness of the device is reduced to 95% at a current density of 10mA/ cm2
  • CIE coordinates are the device at 10mA/ cm2 CIE1931 chromaticity coordinates (x, y) calculated from electroluminescence spectrum at current density.
  • the EQE efficiency and T95 of the device of Compound 1 are 6.8% and 82h, respectively, which is mainly due to the reduction in efficiency and aging of the device due to the aggregation of luminescent molecules (ACS Appl.Mater.Interfaces 2018,10,30022 -30028).
  • the EQE efficiency and T95 lifetime of the device are lower, only 3.6% and 46h, respectively.
  • the performance of its electroluminescent device is significantly improved, especially the efficiency and lifespan.
  • the EQE efficiency of the device embodiment 2 made by applying CH39 can reach 8.9%.
  • the T95 life of the device embodiment 4 made by applying the chemical 94 can reach 129 hours, which is 57% higher than that of the device embodiment 1 and 180% higher than that of the device embodiment 2.
  • Comparative compound 1, comparative compound 2 and CH66 were measured using a spectrofluorophotometer manufactured by Hitachi High-Tech Co., Ltd., a fluorescence spectrometry device, and the test samples were dissolved in a solvent (toluene) (1*10 -5 [mol/L of the concentration] ]), at room temperature (300 [K]), add 360nm excitation light to the sample added in the quartz colorimetric cell, test the fluorescence spectrum, you can get its luminescence peak and half-peak width, as shown in Table 3. Then, the luminescence quantum efficiency (PLQY) of the sample was measured using an absolute PL quantum yield measuring device manufactured by Hamamatsu Photonics.
  • PLQY luminescence quantum efficiency
  • the fluorescence spectrum of the toluene solution of comparative compound-1 is as shown in Figure 2, and its fluorescence peak is 463nm, and luminous efficiency (PLQY) can reach 87%; There are many long-wavelength components, which leads to the color coordinate CIEy of its electroluminescent device as high as 0.15, and the color purity of blue light is not high.
  • the fluorescence spectrum of the toluene solution of comparative compound-2 is shown in Figure 3, and the half-peak width of the fluorescence spectrum is 37nm, which is still relatively broad. However, its fluorescence peak is 428nm, so that the color coordinate CIEy of its electroluminescent device can be as low as 0.04, and the color purity of blue light is high. However, its luminous efficiency (PLQY) is only 56%, resulting in significantly low efficiency and lifetime of the electroluminescent device.
  • the fluorescence spectrum of the toluene solution of 66 of the present invention is shown in Figure 4, the fluorescence peak of its fluorescence spectrum is 457nm, half-maximum width is 21nm, very narrow blue light emission. Therefore, the color coordinate CIEy of its electroluminescent device is as low as 0.07, and the color purity of blue light is high. At the same time, its luminous efficiency (PLQY) is as high as 91%, so that the efficiency and service life of its electroluminescent device are obviously improved.
  • the compound 66 of the present invention has a PLQY and emission wavelength similar to that of the comparative compound 1 of the prior art, but its half-peak width is significantly reduced. At the same time, compared with comparative compound 2, after the molecules of the present invention are connected with aniline units, in addition to the red shift of the luminescence wavelength, the half-peak width is significantly reduced and the luminous efficiency is significantly improved.

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Abstract

La présente invention concerne un composé azacyclique condensé, son utilisation, et un dispositif électroluminescent organique comprenant le composé azacyclique condensé. Le composé azacyclique condensé a une structure d'une combinaison de formules (1) et (2), dans lesquelles Z1 à Z14 sont chacun indépendamment représentés sous la forme de CR1 à CR14 ou N ; lorsque chacun de Z1 à Z14 sur les cycles A à D est indépendamment représenté sous la forme de N, la somme du nombre de Ns sur les cycles A à D est inférieure ou égale à 4 et le nombre de Ns sur chacun des cycles A à D est inférieur ou égal à 1 ; et lorsque la formule (1) est substituée par un groupe substituant représenté par la formule (2), la substitution ne se produit que dans les positions Z1, Z2, Z5, Z6, Z8, Z9, Z12 ou Z13. Le composé selon la présente invention peut être utilisé comme matériau luminescent pour un dispositif électroluminescent organique. Le matériau présente les caractéristiques d'un rendement lumineux élevé et d'un spectre d'émission étroit, et la pureté de couleur lumineuse, l'efficacité lumineuse et la durée de vie du dispositif sont améliorées.
PCT/CN2022/092188 2021-05-20 2022-05-11 Composé azacyclique condensé, son utilisation, et dispositif électroluminescent organique comprenant un composé azacyclique condensé Ceased WO2022242521A1 (fr)

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CN202110551070.6A CN115368370A (zh) 2021-05-20 2021-05-20 一种稠合氮杂环化合物及其应用以及包含该化合物的有机电致发光器件
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Cited By (2)

* Cited by examiner, † Cited by third party
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CN116102560A (zh) * 2023-04-07 2023-05-12 季华实验室 一种三蝶烯化合物、其制备方法和发光器件
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CN121270565A (zh) * 2024-07-02 2026-01-06 季华实验室 一种吡唑啉酮并吩嗪含氮杂环化合物、发光组合物及有机电致发光元件

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