WO2023193775A1 - Matériau électronique organique comprenant du phénanthrène et de la phénanthroline et son utilisation - Google Patents

Matériau électronique organique comprenant du phénanthrène et de la phénanthroline et son utilisation Download PDF

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WO2023193775A1
WO2023193775A1 PCT/CN2023/086685 CN2023086685W WO2023193775A1 WO 2023193775 A1 WO2023193775 A1 WO 2023193775A1 CN 2023086685 W CN2023086685 W CN 2023086685W WO 2023193775 A1 WO2023193775 A1 WO 2023193775A1
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organic
substituted
organic electronic
layer
phenanthroline
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PCT/CN2023/086685
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English (en)
Chinese (zh)
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WO2023193775A8 (fr
Inventor
苏艳
周海涛
吴海发
黄泽甜
谢启燕
张亮
黄珠菊
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上海传勤新材料有限公司
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Publication of WO2023193775A1 publication Critical patent/WO2023193775A1/fr
Publication of WO2023193775A8 publication Critical patent/WO2023193775A8/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—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
    • C07D471/02—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 system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms

Definitions

  • the present invention relates to the technical field of organic electroluminescence, and more specifically, to an organic electronic material containing phenanthrene and o-phenanthroline and its application.
  • OLEDs organic electroluminescent devices
  • OLEDs organic electroluminescent devices
  • LCDs organic electroluminescent devices
  • driving voltage can reduce energy consumption
  • the use of organic materials makes the device It is thinner, lighter and more environmentally friendly
  • the diversified selection of substrates provides the possibility for flexible and transparent displays, which are widely used in mobile phones, flat panel displays, TVs, lighting, vehicle displays and other fields.
  • General organic electroluminescent devices adopt a sandwich structure, that is, the organic layer is sandwiched between the anode and cathode on both sides.
  • the organic layer is divided into a hole transport layer, an electron transport layer, and a light-emitting layer according to the different photoelectric properties of various materials. Hole blocking layer and electron blocking layer, etc.
  • the main luminescence mechanism of the device is: driven by an external voltage, holes and electrons overcome energy barriers and are injected into the hole transport layer and electron transport layer from the anode and cathode respectively, and then recombine and release energy in the luminescent layer, and transfer the energy to organic luminescent substances.
  • the luminescent substance obtains energy and causes it to transition from the ground state to the excited state. When the excited molecules transition to the ground state again, the luminescence phenomenon occurs.
  • Electron transport materials are materials that transport electrons from the cathode to the light-emitting layer. They are an important part of organic electroluminescent devices. They help reduce the injection energy barrier of electrons and avoid Avoid contact between the cathode and the luminescent layer, causing luminescence quenching. Electron transport materials generally require better thermal stability and film-forming properties, higher electron mobility, larger electron affinity and higher excited state energy levels.
  • o-phenanthroline compounds As electron transport materials, they have been used in organic electroluminescent devices. However, the stability of Bphen and BCP, especially the low glass transition temperature, affects the application of o-phenanthroline compounds. As the requirements for OLEDs become higher and higher, there is also a need to develop electron transport materials with excellent thermal stability, film-forming properties and electron transport properties.
  • the present invention provides an organic electronic material containing phenanthrene and o-phenanthroline with high thermal stability, film-forming property and strong electron mobility and its application.
  • the present invention adopts the following technical solution to improve the thermal stability and film-forming properties of the material through substituted phenanthrene groups, and at the same time, introduces pyridine and benzonitrile groups to increase the electron mobility of the material.
  • Its specific structural formula is as follows As shown in formula I,
  • At least one of R 1 and R 2 is one of substituted or unsubstituted pyridyl, benzonitrile, fluorophenyl, and trifluorophenyl, and the other group is hydrogen, deuterium, cyano, C 1 - One of C 10 substituted or unsubstituted alkyl, C 6 -C 30 substituted or unsubstituted aryl, C 3 -C 30 substituted or unsubstituted heteroaryl;
  • L is a single bond, a substituted or unsubstituted aryl group, or one of heteroaryl groups;
  • R 3 is one of hydrogen, deuterium, C 1 -C 10 substituted or unsubstituted alkyl group, C 6 -C 30 substituted or unsubstituted aryl group, C 3 -C 30 substituted or unsubstituted heteroaryl group ;
  • n is an integer from 1 to 6.
  • L is preferably a single bond, phenyl, naphthyl or biphenyl.
  • R3 is preferably hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, phenyl, tolyl, biphenyl or naphthyl.
  • the organic electronic material containing phenanthrene and o-phenanthroline includes but is not limited to any one of the following compounds 1-120.
  • organic electronic materials containing phenanthrene and o-phenanthroline can be used in organic electroluminescent devices, which include an anode, a cathode and an organic layer.
  • the organic layer includes at least one of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer or an electron transport layer; at least one layer of the organic layer contains organic electrons of the above formula I Material.
  • the electron transport layer or electron injection layer in the organic layer contains the organic electronic material of Formula I above.
  • the hole blocking layer in the organic layer contains the above-mentioned organic electronic material.
  • the electron transport layer in addition to the compound represented by formula I, it can also be doped with organic metal complexes, such as lithium 8-hydroxyquinolate, in which the doping mass content of the metal complex is 20-70%.
  • the total thickness of the organic layer is 1-1000 nm; further preferably, the total thickness of the organic layer is 50-500 nm.
  • Each layer of the organic layer in the organic electroluminescent device can be formed by vacuum evaporation, molecular beam evaporation, solvent-soluble dip coating, spin coating, rod coating, or inkjet printing.
  • Preparation method the metal electrode can be prepared by evaporation method or sputtering method.
  • the organic electronic materials shown in Formula I can also be used to produce organic solar cells, organic thin film transistors, organic photodetectors, organic field effect transistors, organic integrated circuits or organic photoreceptors.
  • the invention provides an organic electron transmission material containing phenanthrene and o-phenanthroline. Since the phenanthrene containing substituents improves the thermal stability of the compound, the improvement of thermal stability can improve the film-forming property of the material and reduce the preparation time. The morphology of the semiconductor layer of the device deteriorates. At the same time, an o-phenanthroline group is introduced, and a pyridyl group and a benzonitrile group are introduced into the phenanthrene to improve the electron transmission performance of the material. When used as an electron transmission material in blue organic electroluminescent devices, it can improve the high luminous efficiency of the device and extend the life of the device. Service life, which is important for, for example, power consumption reduction and battery life extension of mobile display devices.
  • Figure 1 is the DSC chart of compound 1.
  • Figure 2 is the DSC chart of compound 11.
  • Figure 3 is the DSC chart of compound 61.
  • Figure 4 is the DSC chart of compound 72.
  • Figure 5 is the DSC chart of compound 91.
  • Figure 6 is a schematic diagram of the device structure.
  • Figure 7 is a graph showing the relationship between voltage and current density of devices prepared with compounds of the present invention.
  • Figure 8 is a graph showing the relationship between current density and current efficiency of devices prepared with compounds of the present invention.
  • Figure 9 is a graph showing the relationship between current density and power efficiency of devices prepared with compounds of the present invention.
  • the glass transition temperature (Tg) of the compound was tested using a differential scanning calorimeter Pyris Diamond (DSC 2920) under nitrogen protection at a heating and cooling rate of 10°C/min.
  • the glass transition temperature of the compound of the present invention reaches 118-161 degrees, which is significantly higher than that of BCP and Bphen, showing that the compound has good thermal stability.
  • FIG. 6 Preparation of organic electroluminescent devices, the structural schematic diagram is shown in Figure 6.
  • the specific device structure is as follows: glass/anode (ITO)/hole injection layer (HIL)/hole transport layer (HTL)/electron blocking layer (EBL)/luminescence Layer (EML, host material BH: blue luminescent material BD, 97: 3)/Electron transport layer (ETL, electron transport material: 8-hydroxyquinoline lithium, 50:50)/Electron injection layer (EIL)/Cathode (Mg:Ag, 9:1)
  • Compound 1 prepared in Example 1 was used to prepare OLED.
  • the transparent conductive ITO glass substrate 110 (with the anode 120 on it) (China Southern Glass Group Co., Ltd.) is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, and then washed with ethanol, acetone and deionized water in sequence. Bake in a clean environment until the moisture is completely removed, clean with ultraviolet photosynthetic ozone, and then treat with oxygen plasma for 30 seconds.
  • HIL hole injection layer 130 on the ITO at a evaporation rate of 0.1 nm/s.
  • Compound HT is evaporated on the hole injection layer to form a hole transport layer 140 with a thickness of 80 nm, and the evaporation rate is 0.1 nm/s.
  • EB is evaporated on the empty transport layer to form a 10 nm thick electron blocking layer 150 .
  • the evaporation rate is 0.1nm/s.
  • a 30 nm thick light-emitting layer 160 was evaporated on the hole blocking layer, in which BH was the host light-emitting material, and BD with a weight ratio of 3% was used as the doped guest material.
  • the evaporation rate was 0.1 nm/s.
  • a 35 nm thick mixture of 50% by weight Compound 1 and 50% by weight LiQ was evaporated on the light-emitting layer as the electron transport layer 170 .
  • the evaporation rate is 0.1nm/s.
  • LiQ was evaporated to a thickness of 1 nm as the electron injection layer 180 on the electron transport layer.
  • Example 9 The only difference from Example 9 is that Compound 1 of the electron transport material is replaced by other compounds of the present invention.
  • the specific device structure is as follows in Table 1.
  • Example 9 The only difference from Example 9 is that Compound 1 of the electron transport material was replaced with Comparative Compound BCP.
  • the specific device structure is as follows in Table 1.
  • the above-mentioned organic materials are all existing known materials and are purchased from the market.
  • the prepared device was measured with a Photo Research PR655 spectrometer for operating voltage, current efficiency, emission spectrum, and power efficiency, as well as the lifetime (T95) of the brightness attenuating to 95% of the original brightness at a current density of 20 mA/ cm2 .
  • Figure 7 is a relationship diagram between voltage and current density in Examples 9-14.
  • Figures 8 and 9 are relationship diagrams between current density and efficiency in Examples 9-14.
  • Table 2 shows the voltage and current density at a current density of 20mA/cm. Efficiency and lifespan are shown in Table 2.
  • the device prepared by the present invention using compounds based on phenanthrene and o-phenanthroline as electron transmission materials has significantly improved current efficiency and power efficiency, and the same current density
  • the voltage under the condition is reduced, and the service life is also significantly improved.
  • the compound of the present invention shows excellent performance, and the performance of the amorphous film improves the performance of the device.

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un matériau électronique organique comprenant du phénanthrène et de la phénanthroline et son utilisation. La formule spécifique développée est telle que représentée par la formule suivante I, <img file="PCTCN2023086685-isre-I000001.jpg" he="37.76" img-content="drawing" img-format="jpg" inline="yes" orientation="portrait" wi="66.07"/>. Dans la formule I, au moins l'un de R1 et R2 est l'un parmi pyridyle, benzonitrile, fluorophényle et trifluorophényle substitué ou non substitué, et l'autre groupe est l'un parmi hydrogène, deutérium, cyano, alkyle en C1-C10 substitué ou non substitué, aryle en C6-C30 substitué ou non substitué et hétéroaryle en C3-C30 substitué ou non substitué; L est l'un parmi une liaison simple, aryle substitué ou non substitué et hétéroaryle; R3 est l'un parmi hydrogène, deutérium, alkyle en C1-C10 substitué ou non substitué, aryle en C6-C30 substitué ou non substitué, et hétéroaryle en C3-C30 substitué ou non substitué; n est un nombre entier de 1 à 6.
PCT/CN2023/086685 2022-04-07 2023-04-06 Matériau électronique organique comprenant du phénanthrène et de la phénanthroline et son utilisation WO2023193775A1 (fr)

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CN202210363765.6 2022-04-07
CN202210363765.6A CN114702489A (zh) 2022-04-07 2022-04-07 一种含有菲和邻菲罗啉的有机电子材料及其应用

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CN114702489A (zh) * 2022-04-07 2022-07-05 上海传勤新材料有限公司 一种含有菲和邻菲罗啉的有机电子材料及其应用
CN115448899A (zh) * 2022-09-30 2022-12-09 深圳市华星光电半导体显示技术有限公司 蒽类化合物、混合物、组合物以及有机电子器件

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CN112514097A (zh) * 2018-07-18 2021-03-16 诺瓦尔德股份有限公司 化合物以及包含所述化合物的有机半导体层、有机电子器件、显示装置和照明装置
CN114702489A (zh) * 2022-04-07 2022-07-05 上海传勤新材料有限公司 一种含有菲和邻菲罗啉的有机电子材料及其应用

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KR20200064423A (ko) * 2018-11-29 2020-06-08 주식회사 진웅산업 파이렌 화합물 및 이를 포함하는 유기발광소자
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