WO2019218970A1 - Dispositif électroluminescent organique à fluorescence retardée activé thermiquement - Google Patents

Dispositif électroluminescent organique à fluorescence retardée activé thermiquement Download PDF

Info

Publication number
WO2019218970A1
WO2019218970A1 PCT/CN2019/086678 CN2019086678W WO2019218970A1 WO 2019218970 A1 WO2019218970 A1 WO 2019218970A1 CN 2019086678 W CN2019086678 W CN 2019086678W WO 2019218970 A1 WO2019218970 A1 WO 2019218970A1
Authority
WO
WIPO (PCT)
Prior art keywords
organic compound
organic
electroluminescent device
layer
level
Prior art date
Application number
PCT/CN2019/086678
Other languages
English (en)
Chinese (zh)
Inventor
李崇
赵鑫栋
张兆超
叶中华
Original Assignee
江苏三月光电科技有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 江苏三月光电科技有限公司 filed Critical 江苏三月光电科技有限公司
Publication of WO2019218970A1 publication Critical patent/WO2019218970A1/fr

Links

Images

Classifications

    • 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
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/20—Delayed fluorescence emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/40—Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
    • 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

Definitions

  • the present invention relates to the field of semiconductor technology, and in particular to an organic electroluminescent device.
  • Organic electroluminescent devices based on thermally activated delayed fluorescent materials have become a hotspot of research and development due to their low material synthesis difficulty, no need to use precious metals, and high purity of luminescent color. It is considered to have great application potential in the field of next-generation flat panel display. In recent years, it has received extensive attention.
  • the basic structure of an organic electroluminescent device comprises an opposite cathode and an anode, and a light-emitting layer sandwiched between the cathode and the anode.
  • the light-emitting layer generally requires the host material to be doped with a guest material to obtain more efficient energy transfer efficiency, and fully utilize the luminescent potential of the guest material.
  • Thermally activated delayed fluorescence (TADF) materials are the third generation of organic luminescent materials developed after organic fluorescent materials and organic phosphorescent materials.
  • the thermally activated delayed fluorescent material has a small triplet state and a singlet energy difference, which facilitates the realization of anti-intersystem enthalpy, reduces the triplet exciton concentration, reduces the exciton quenching probability, and fully utilizes the single line formed under electrical excitation.
  • the internal quantum efficiency of the device can reach 100%.
  • the material structure is controllable, the property is stable, the price is cheap, no precious metal is needed, and the application prospect in the field of OLEDs is broad.
  • the present invention provides a high efficiency organic electroluminescent device in view of the problems existing in the prior art.
  • the organic electroluminescent device provided by the invention can realize multi-channel energy transfer between host and guest, improve the utilization of excitons inside the device, reduce the probability of exciton quenching, and effectively improve the efficiency and stability of the organic electroluminescent device.
  • An organic electroluminescent device comprising a light-emitting layer comprising a host material and a guest material, the host material comprising at least one first organic compound and at least one second organic compound, the guest material being phosphorescent a compound or a fluorescent compound;
  • the difference between the singlet level and the triplet level of the first organic compound is not more than 0.2 eV, preferably not more than 0.15 eV, more preferably not more than 0.1 eV;
  • the difference between the singlet level and the triplet level of the second organic compound is not more than 0.2 eV, preferably not more than 0.15 eV, more preferably not more than 0.1 eV;
  • the singlet energy level of the first organic compound is smaller than the triplet energy level of the second organic compound, and the difference is not less than 0.1 eV, preferably not less than 0.15 eV, more preferably not less than 0.2 eV;
  • the difference between the HOMO level and the LUMO level of the second organic compound is not less than 2.8 eV, preferably not less than 3.0 eV, more preferably not less than 3.2 eV.
  • the first organic compound is a compound having a D-A structure or a D- ⁇ -A structure.
  • the second organic compound is a compound having a D-A structure or a D- ⁇ -A structure.
  • the first organic compound is selected from one of the following compounds:
  • the second organic compound is selected from one of the following compounds:
  • the weight ratio of the first organic compound to the second organic compound is from 9:1 to 1:9, preferably from 7:3 to 3:7, more preferably from 6:4 to 4:6.
  • the fluorescent compound comprises a thermally activated delayed fluorescent material, wherein the singlet state level and the triplet level difference of the thermally activated delayed fluorescent material are not more than 0.2 eV, preferably not more than 0.15 eV, more preferably not more than 0.1 eV.
  • the singlet state energy level of the thermally activated delayed fluorescent material is smaller than the triplet energy level of the first organic compound, and the difference is not less than 0.1 eV, preferably not less than 0.15 eV.
  • the weight of the guest material relative to the weight of the host material is from 0.5 to 20% by weight, preferably from 1 to 15% by weight, more preferably from 3 to 12% by weight, based on the weight of the host material.
  • the organic electroluminescent device provided by the present application further includes a hole transporting region and an electron transporting region, the hole transporting region comprising one or more of a hole injecting layer, a hole transporting layer, and an electron blocking layer.
  • the electron transporting region comprises a combination of one or more of an electron injecting layer, an electron transporting layer, and a hole blocking layer.
  • the application also provides an illumination or display element comprising an organic electroluminescent device as described above.
  • the host material of the light-emitting layer is composed of two materials, wherein the first compound is a thermally activated delayed fluorescent material having a small singlet-triplet level difference ( ⁇ Est).
  • the second organic compound is also a thermally activated delayed fluorescent material having a smaller singlet-triplet level difference ([Delta]Est).
  • the thermally activated delayed fluorescent material can achieve effective reverse intersystem crossing, reduce the triplet exciton concentration of the host material, reduce the probability of triplet exciton quenching, and improve device stability.
  • the first organic compound and the second organic compound are both thermally activated delayed fluorescent materials, having a small triplet state and a singlet energy difference
  • the first organic compound can transfer energy from the triplet state to the singlet state through the anti-intersystem enthalpy. Then, from the singlet state, the Forster energy transfer is transferred to the singlet energy level of the guest material, and the triplet energy of the first organic compound can also be transferred to the triplet energy level of the guest material through the Dexter energy transfer.
  • the exciton energy in the second organic compound can also be transitioned from the triplet state to the singlet state by the anti-systemic enthalpy, and then transmitted to the first organic compound and the singlet energy level of the guest material through the Forster energy transfer, while the second organic compound
  • the triplet energy can also be transferred to the first organic compound and the triplet energy level of the guest material through Dexter energy transfer to achieve multi-channel energy transfer, as shown in Figure 1.
  • the second compound in the present invention is a compound having a wider band gap, and the second organic compound having a wide band gap can dilute the first organic compound, reducing the quenching effect of the first organic compound due to agglomeration.
  • the T1 energy level of the second organic compound in the invention is higher than the S1 energy level of the first organic compound, which can effectively prevent energy return between the first organic compound and the second organic compound, improve energy utilization, and further improve The efficiency and stability of the device.
  • the invention provides that the light-emitting layer of the organic electroluminescent device can improve the efficiency of the organic electroluminescent device and reduce the roll-off of efficiency, and has good application effects and industrialization prospects.
  • Figure 1 is a schematic diagram of energy transfer between host and guest.
  • FIG. 2 is a schematic view of an embodiment of an organic electroluminescent device, wherein: 1, a substrate layer; 2, an anode layer; 3, a hole injection layer 4, a hole transport layer; 5, an electron blocking layer; 7, hole blocking / electron transport layer; 8, electron injection layer; 9, cathode layer.
  • Fig. 3 is a graph showing changes in device voltage with time at an initial luminance of 5000 cd/m 2 .
  • Figure 4 shows the variation of the EQE of the device at different temperatures.
  • HOMO means the highest occupied orbital of a molecule
  • LUMO means the lowest unoccupied orbital of a molecule
  • the "HOMO level and LUMO level difference" referred to in the present specification means the difference of the absolute values of each energy value.
  • the HOMO and LUMO energy levels are represented by absolute values, and the comparison between energy levels is also the magnitude of the absolute value thereof, and those skilled in the art know that the greater the absolute value of the energy level, the energy The lower the energy of the stage.
  • not greater than in the present invention means less than or equal to, unless otherwise stated, “not less than” means greater than or equal to, and there are no upper and lower limits.
  • the singlet (S1) level means the singlet state of the lowest excited state level of the molecule
  • the triplet (T1) level means the lowest excited level of the triplet state of the molecule.
  • the "triplet level difference” and “single line state and triplet level difference” referred to in the present specification mean the difference of the absolute values of each energy value.
  • the difference between the energy levels is expressed in absolute values.
  • the singlet and triplet levels can be measured by fluorescence and phosphorescence spectroscopy, respectively, as is well known to those skilled in the art.
  • the selection of the first organic compound and the second organic compound constituting the host material is not particularly limited as long as the singlet and triplet energy levels thereof and the LUMO level and the HOMO level difference satisfy the above conditions.
  • the first organic compound is selected from the group consisting of compounds of the formula:
  • the second organic compound is selected from the group consisting of compounds of the formula:
  • the weight ratio of the first organic compound to the second organic compound constituting the host material is not particularly limited. There is no particular restriction on the choice of guest materials. There is no particular limitation on the weight ratio of the constituent host material to the guest material. In a preferred embodiment, the guest material is selected from compounds having the formula:
  • electrons are injected from a cathode and transported to a light-emitting layer, and holes are injected from an anode and transmitted to a light-emitting layer.
  • the first electrode can be an anode and the second electrode can be a cathode.
  • the anode comprises a metal, a metal oxide or a conductive polymer.
  • the anode can have a work function in the range of about 3.5 to 5.5 eV.
  • conductive materials include carbon, aluminum, vanadium, chromium, copper, zinc, silver, gold, other metals, and alloys thereof; zinc oxide, indium oxide, tin oxide, indium tin oxide (ITO), indium zinc oxide, and others. Similar metal oxides; and mixtures of oxides and metals, such as ZnO:Al and SnO 2 :F.
  • Both transparent and non-transparent materials can be used as the anode material.
  • a transparent anode can be formed.
  • the transparency means the extent to which light emitted from the organic material layer is permeable, and the light transmittance is not particularly limited.
  • the organic light-emitting device of the present specification is of a top emission type, and an anode is formed on a substrate before the organic material layer and the cathode are formed, not only a transparent material but also a non-transparent material having excellent light reflectivity can be used as the anode material.
  • a transparent material is required as the anode material, or the non-transparent material needs to be formed as A film that is thin enough to be transparent.
  • a material having a small work function is preferable as the cathode material so that electron injection can be easily performed.
  • a material having a work function ranging from 2 eV to 5 eV can be used as the cathode material.
  • the cathode may comprise a metal such as magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin and lead or alloys thereof; a material having a multilayer structure such as LiF/Al or LiO 2 / Al, etc., but is not limited to this.
  • the cathode can be formed using the same material as the anode.
  • the cathode can be formed using an anode material as described above.
  • the cathode or anode can comprise a transparent material.
  • the organic light-emitting device of the present invention may be of a top emission type, a bottom emission type, or a two-side emission type depending on the material used.
  • the organic light-emitting device of the present invention comprises a hole transport layer.
  • the hole transport layer may preferably be interposed between the hole injection layer and the light-emitting layer or between the anode and the light-emitting layer.
  • the hole transport layer is formed of a hole transport material known to those skilled in the art.
  • the hole transporting material is preferably a material having a high hole mobility capable of transferring holes from the anode or the hole injecting layer to the light emitting layer.
  • Specific examples of the hole transporting material include, but are not limited to, an aromatic amine-based organic material, a conductive polymer, and a block copolymer having a joint portion and a non-joining portion.
  • the organic light-emitting device of the present invention further comprises an electron blocking layer.
  • the electron blocking layer may preferably be disposed between the hole transport layer and the light emitting layer, or between the hole injection layer and the light emitting layer, or between the anode and the light emitting layer.
  • the electron blocking layer is formed of an electron blocking material known to those skilled in the art, such as TCTA.
  • the organic light-emitting device of the present invention comprises an electron injecting layer.
  • the electron injecting layer may preferably be placed between the cathode and the luminescent layer.
  • the electron injecting layer is formed of an electron injecting material known to those skilled in the art.
  • the electron injecting layer can be formed using, for example, an electron accepting organic compound.
  • an electron accepting organic compound a known optional compound can be used without particular limitation.
  • a polycyclic compound such as p-terphenyl or tetraphenyl or a derivative thereof; a polycyclic hydrocarbon compound such as naphthalene, naphthacene, anthracene, hexabenzobenzene, fluorene, fluorene, or the like can be used.
  • Phenylhydrazine or phenanthrene, or a derivative thereof; or a heterocyclic compound for example, phenanthroline, phenanthroline, phenanthridine, acridine, quinoline, quinoxaline or phenazine, or a derivative thereof.
  • inorganic materials including, but not limited to, for example, magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin, and lead or alloys thereof; LiF, LiO 2 , LiCoO 2 , NaCl, MgF 2 , CsF, CaF 2 , BaF 2 , NaF, RbF, CsCl, Ru 2 CO 3 , YbF 3 , etc.; and a material having a multilayer structure such as LiF/Al or LiO 2 /Al.
  • inorganic materials including, but not limited to, for example, magnesium, calcium, sodium, potassium, titanium, indium, lanthanum, lithium, lanthanum, aluminum, silver, tin, and lead or alloys thereof; LiF, LiO 2 , LiCoO 2 , NaCl, MgF 2 , CsF, CaF 2 , BaF 2 , NaF, RbF, CsCl, Ru 2
  • the organic light emitting device of the present invention comprises an electron transport layer.
  • the electron transport layer may preferably be disposed between the electron injecting layer and the light emitting layer, or between the cathode and the light emitting layer.
  • the electron transport layer is formed of an electron transport material known to those skilled in the art.
  • the electron transporting material is a material capable of easily receiving electrons from the cathode and transferring the received electrons to the light emitting layer. Materials having high electron mobility are preferred.
  • Specific examples of the electron transporting material include, but are not limited to, an 8-hydroxyquinoline aluminum complex; a composite containing Alg 3 ; an organic radical compound; and a hydroxyflavone metal complex; and TPBi.
  • the organic light-emitting device of the present invention further comprises a hole blocking layer.
  • the hole blocking layer may preferably be disposed between the electron transport layer and the light emitting layer, or between the electron injecting layer and the light emitting layer, or between the cathode and the light emitting layer.
  • the hole blocking layer is a layer that prevents the injected holes from passing through the light emitting layer to the cathode, and can be generally formed under the same conditions as the hole injection layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • the hole blocking layer can be the same layer as the electron transport layer.
  • the organic light emitting device may further include a substrate.
  • the first electrode or the second electrode may be provided on the substrate.
  • the substrate can be a rigid substrate, such as a glass substrate, or a flexible substrate, such as a flexible film-shaped glass substrate, a plastic substrate, or a film-shaped substrate.
  • the organic light-emitting device of the present invention can be produced using the same materials and methods known in the art.
  • the organic light-emitting device of the present invention can be fabricated by sequentially depositing a first electrode, one or more organic material layers, and a second electrode on a substrate.
  • the organic light emitting device can be produced by depositing a metal, a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method (for example, sputtering or electron beam evaporation) to form an anode;
  • PVD physical vapor deposition
  • An organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer is formed on the anode; a material that can be used to form a cathode is then deposited thereon.
  • the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, one or more organic material layers, and an anode material on a substrate.
  • the organic light-emitting composite material of the present invention may be formed into an organic material layer using a solution coating method.
  • solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roll coating, and the like, but is not limited thereto.
  • the thickness of the light-emitting layer and optionally the hole injection layer, the hole transport layer, the electron block layer, and the electron transport layer, the electron injection layer are each from 0.5 to 150 nm, preferably from 1 to 100 nm.
  • the luminescent layer has a thickness of from 20 to 80 nm, preferably from 30 to 50 nm.
  • An organic electroluminescent device comprising the organic light-emitting composite material of the present invention has an advantage in that the device is more efficient and has a longer life.
  • the structure of the organic electroluminescent device prepared in Example 1 is shown in FIG. 2, and the specific preparation process of the device is as follows:
  • the ITO anode layer 2 on the transparent glass substrate layer 1 was cleaned, ultrasonically washed with deionized water, acetone, and ethanol for 15 minutes, respectively, and then treated in a plasma cleaner for 2 minutes; the ITO glass substrate was dried and placed in a vacuum. In the cavity, the vacuum degree is less than 2*10 -6 Torr, and 10 nm thick HAT-CN is deposited on the ITO anode layer 2, and the layer is used as the hole injection layer 3; then 80 nm of HT1 is evaporated, and the layer is empty.
  • HI1 HOMO is 5.9 eV, LUMO is 3.0 eV, S1 is 2.79 eV, and T1 is 2.72 eV;
  • HI2 HOMO is 5.82 eV
  • LUMO is 2.8 eV
  • S1 is 2.82 eV
  • T1 is 2.77 eV;
  • HI5 HOMO is 5.65 eV, LUMO is 2.84 eV, S1 is 2.76 eV, and T1 is 2.74 eV;
  • HI13 HOMO is 5.86eV, LUMO is 3.09eV, S1 is 2.78eV, and T1 is 2.71eV;
  • HI16 HOMO is 5.63 eV, LUMO is 2.82 eV, S1 is 2.79 eV, and T1 is 2.71 eV;
  • HII12 HOMO is 5.68 eV, LUMO is 2.66 eV, S1 is 2.89 eV, and T1 is 2.88 eV;
  • HII16 HOMO is 6.48eV, LUMO is 2.89eV, S1 is 3.06eV, and T1 is 2.89eV;
  • HII23 HOMO is 5.79 eV, LUMO is 2.52 eV, S1 is 3.05 eV, and T1 is 2.97 eV;
  • HII24 HOMO is 5.95 eV, LUMO is 2.85 eV, S1 is 3.02 eV, and T1 is 2.92 eV;
  • DP-1 HOMO is 5.41 eV, LUMO is 2.71 eV, S1 is 2.62 eV, and T1 is 2.45 eV;
  • DP-2 HOMO is 5.51 eV, LUMO is 2.9 eV, S1 is 2.61 eV, and T1 is 2.48 eV;
  • the organic electroluminescent devices prepared in Examples 1 to 60 and Comparative Examples 1 to 18 were tested for performance.
  • the test method was as follows: the HOMO level was measured by an IPS-3 ionization energy measurement system, and the measurement steps were as follows: on ITO full glass.
  • the sample film was vapor-deposited at 60 nm; the sample was placed in the sample stage of the IPS-3 ionization energy test system, and vacuum was applied to 5 ⁇ 10 -2 Pa; a voltage was applied to the sample, and electrons were emitted from the surface of the sample to be fed back in the form of current;
  • the fitting obtains the ionization energy of the electron, which is the HOMO value of the sample.
  • the LUMO energy level is calculated by indirectly measuring the sample band gap.
  • the S1 level and the T1 level are obtained by measuring the sample normal temperature and the low temperature PL spectrum.
  • the measurement steps are as follows: a mixed single film of the above materials is prepared in a vacuum evaporation chamber, and then the normal temperature PL spectrum and the low temperature PL spectrum of the above single film are respectively measured.
  • the normal temperature PL spectrum is irradiated onto the surface of the sample by a 325 nm laser light source, and the emitted light is detected to obtain the peak wavelength of the excitation spectrum.
  • the low-temperature PL spectrum was obtained by cooling the sample to 35 K, and irradiating the surface of the sample with a laser light source of 325 nm to detect the emitted light to obtain the peak wavelength of the excitation spectrum.
  • the attenuation ratios are all large, both approaching or exceeding 10%.
  • the main reason for this is because the triplet excitons are quenched by the easy aggregation of the fluorescent material with a single thermal activation.
  • there is only a single energy transfer channel between the host and the guest which tends to result in higher exciton concentration and severe exciton quenching, which seriously affects the efficiency and stability of the device under high brightness.
  • the first organic compound and the second organic compound are mixed to form a host material, and the first organic compound can transfer energy from the triplet state to the singlet state through the anti-systemic enthalpy, and then pass through the singlet state through the Forster Energy transfer is transferred to the guest material.
  • the second organic compound excitons can also transition from the triplet state to the singlet state through the inter-system enthalpy, and then pass through the Forster energy transfer to the first organic compound and the guest material to achieve multi-channel energy transfer.
  • the second compound in the present invention is a compound having a wider band gap, and the second organic compound having a wide band gap can dilute the first organic compound, suppressing the Dexter energy transfer between the first organic compound and the guest material, and reducing the first organic compound due to The quenching effect brought about by agglomeration.
  • the T1 energy level of the second organic compound in the invention is higher than the S1 energy level of the first organic compound, which can effectively prevent energy return between the first organic compound and the second organic compound, improve energy utilization, and further improve The efficiency and stability of the device.
  • the present invention was tested at an initial luminance of 5000cd / m 2, the voltage change over time of the device, the device of Comparative Example 1, Example 1, Comparative Example 5, Example 15 Comparative example 7,
  • Example 37 Comparative Example 14, and Example 50 were tested. The results are shown in Table 3 and Figure 3.
  • the device applied in the present invention changes the device voltage at about 300 volts at 5000 cd/m 2 over time, and the device in the comparative example is in the comparative example.
  • the variation exceeds 0.6V or even higher, indicating that the stability of the device is better at higher brightness.
  • the device to which the present invention is applied has a small change in device EQE at different temperatures compared with the conventional device, and at a relatively high temperature, the device EQE has almost no The change indicates that the device with the structure of the present application has better device stability.

Landscapes

  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un dispositif électroluminescent organique à fluorescence retardée activé thermiquement, comprenant une couche électroluminescente. La couche électroluminescente comprend au moins un premier composé organique et au moins un second composé organique en tant que matériaux hôtes, et un composé phosphorescent ou un composé fluorescent en tant que matériau invité. Le dispositif électroluminescent organique selon l'invention présente un rendement lumineux élevé et un faible affaiblissement.
PCT/CN2019/086678 2018-05-14 2019-05-13 Dispositif électroluminescent organique à fluorescence retardée activé thermiquement WO2019218970A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201810457062.3A CN110492008B (zh) 2018-05-14 2018-05-14 一种热活化延迟荧光有机电致发光器件
CN201810457062.3 2018-05-14

Publications (1)

Publication Number Publication Date
WO2019218970A1 true WO2019218970A1 (fr) 2019-11-21

Family

ID=68539483

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2019/086678 WO2019218970A1 (fr) 2018-05-14 2019-05-13 Dispositif électroluminescent organique à fluorescence retardée activé thermiquement

Country Status (2)

Country Link
CN (1) CN110492008B (fr)
WO (1) WO2019218970A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111100072A (zh) * 2019-11-28 2020-05-05 吉林奥来德光电材料股份有限公司 一种有机光电化合物、其合成方法及有机电致发光器件

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103922995A (zh) * 2014-04-08 2014-07-16 上海天马有机发光显示技术有限公司 一种有机电致发光器件及显示装置
US20150155511A1 (en) * 2013-12-02 2015-06-04 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display module, lighting module, light-emitting device, display device, electronic appliance, and lighting device
CN104716268A (zh) * 2013-12-17 2015-06-17 北京维信诺科技有限公司 一种有机电致发光器件及其制备方法
CN106206958A (zh) * 2015-04-30 2016-12-07 北京维信诺科技有限公司 一种白光有机电致发光器件
CN106206997A (zh) * 2015-04-29 2016-12-07 北京维信诺科技有限公司 一种有机电致发光器件
CN106467458A (zh) * 2016-07-27 2017-03-01 江苏三月光电科技有限公司 一种基于二芳基酮的化合物及其在有机电致发光器件上的应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105503766B (zh) * 2015-12-18 2018-06-22 昆山国显光电有限公司 一种热活化延迟荧光材料及有机电致发光器件

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150155511A1 (en) * 2013-12-02 2015-06-04 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display module, lighting module, light-emitting device, display device, electronic appliance, and lighting device
CN104716268A (zh) * 2013-12-17 2015-06-17 北京维信诺科技有限公司 一种有机电致发光器件及其制备方法
CN103922995A (zh) * 2014-04-08 2014-07-16 上海天马有机发光显示技术有限公司 一种有机电致发光器件及显示装置
CN106206997A (zh) * 2015-04-29 2016-12-07 北京维信诺科技有限公司 一种有机电致发光器件
CN106206958A (zh) * 2015-04-30 2016-12-07 北京维信诺科技有限公司 一种白光有机电致发光器件
CN106467458A (zh) * 2016-07-27 2017-03-01 江苏三月光电科技有限公司 一种基于二芳基酮的化合物及其在有机电致发光器件上的应用

Also Published As

Publication number Publication date
CN110492008B (zh) 2020-06-12
CN110492008A (zh) 2019-11-22

Similar Documents

Publication Publication Date Title
CN110498790B (zh) 有机发光复合材料和含有其的有机电致发光器件
CN110492005B (zh) 一种以激基复合物作为主体材料的有机电致发光器件
Gao et al. Bright-blue electroluminescence from a silyl-substituted ter-(phenylene–vinylene) derivative
WO2020034805A1 (fr) Dispositif électroluminescent organique à base de système exciplexe et excimère
CN110492006B (zh) 一种基于含硼有机化合物的电致发光器件
TWI441898B (zh) 有機ｅｌ元件
WO2019218969A1 (fr) Dispositif électroluminescent basé sur un système exciplexe avec des composés organiques contenant du bore
WO2019128951A1 (fr) Matériau composite électroluminescent organique et dispositif électroluminescent organique le comprenant
CN110010783B (zh) 一种串联式有机电致发光器件
CN109378392B (zh) 一种有机电致发光器件及显示装置
CN110957435B (zh) 一种基于tta延迟荧光的有机电致发光器件
CN110010784B (zh) 一种含有多通道载流子传输材料的全色有机电致发光器件
EP2284921A2 (fr) Élément électroluminescent organique
JP2007096023A (ja) 有機発光素子
CN107021939A (zh) 基于苯并噻二唑的d‑a‑a型近红外发光化合物及其应用
WO2019218970A1 (fr) Dispositif électroluminescent organique à fluorescence retardée activé thermiquement
CN106008574B (zh) 一种用作有机电致磷光器件主体材料和热致延迟荧光材料的多功能化三芳基硼衍生物
CN111668379B (zh) 一种含芘或氮杂芘的有机电致发光器件
CN111697145B (zh) 非掺杂溶液加工型树枝状热活化延迟荧光电致发光二极管
CN112490390B (zh) 一种新型hit、eb材料搭配的有机电致发光器件
CN111864093B (zh) 一种用于电子传输层的组合物、电子传输层及光电器件
WO2023201651A1 (fr) Dispositif électroluminescent organique et appareil d'affichage
CN110957424B (zh) 多光谱oled器件及其制备方法
KR20220081707A (ko) 유기 발광 소자
CN117441422A (zh) 包括基底、阳极层、阴极层、至少一个第一发光层和至少一个包含金属络合物的空穴注入层的有机电子器件

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19804294

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19804294

Country of ref document: EP

Kind code of ref document: A1