WO2022242584A1 - Organic electroluminescent device and display apparatus - Google Patents
Organic electroluminescent device and display apparatus Download PDFInfo
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- WO2022242584A1 WO2022242584A1 PCT/CN2022/092948 CN2022092948W WO2022242584A1 WO 2022242584 A1 WO2022242584 A1 WO 2022242584A1 CN 2022092948 W CN2022092948 W CN 2022092948W WO 2022242584 A1 WO2022242584 A1 WO 2022242584A1
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- -1 bipyridyl compound Chemical class 0.000 claims abstract description 102
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- 229910052805 deuterium Inorganic materials 0.000 claims description 8
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- 125000003118 aryl group Chemical group 0.000 claims description 7
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- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
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- 125000004429 atom Chemical group 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000001748 luminescence spectrum Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
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- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
Definitions
- the invention relates to an organic electroluminescence device and a display device, belonging to the technical field of organic electroluminescence.
- Organic Light Emitting Diode (Organic Light Emitting Diode, referred to as OLED) is a device that is driven by current to achieve the purpose of emitting light. Its main characteristics come from the organic light-emitting layer. When an appropriate voltage is applied, electrons and holes Excitons are combined in the organic light-emitting layer to emit light of different wavelengths according to the characteristics of the organic light-emitting layer.
- the light-emitting layer is composed of host materials and doped dyes, and the dyes are mostly selected from traditional fluorescent materials and phosphorescent materials. Specifically, traditional fluorescent materials have the disadvantage of not being able to utilize triplet excitons.
- phosphorescent materials can achieve 100% energy use efficiency by introducing heavy metal atoms, such as iridium or platinum, to realize the transition from singlet excitons to triplet states, but Heavy metals such as iridium or platinum are very scarce, expensive and easily cause environmental pollution, so phosphorescent materials cannot be the first choice for dyes.
- Thermally activated delayed fluorescent materials can realize reverse intersystem jumping from triplet excitons to singlet states by absorbing ambient heat, and then emit fluorescence from singlet states.
- the lifetime of triplet excitons in TADF materials is long, and the device efficiency drops Large drop, poor stability and other shortcomings.
- the purpose of the present invention is to provide an organic electroluminescence device, the organic light-emitting layer of the device uses a wide bandgap material as the main material, doped with a boron-nitrogen compound of a specific structure as a luminescent dye, and realizes 100% exciton utilization, thereby improving the efficiency and stability of organic light-emitting devices.
- An organic electroluminescent device comprising a first electrode, a second electrode and an organic functional layer
- the organic functional layer includes an organic light-emitting layer
- the organic light-emitting layer includes a host material and a luminescent dye
- the host material is Wide bandgap material
- the singlet energy level (S 1 h ) of the host material is greater than the singlet energy level (S 1 g ) of the luminescent dye
- the triplet energy level (T 1 h ) of the host material is greater than or equal to the second triplet energy level (T 2 g ) of the luminescent dye
- the second triplet energy level (T 2 g ) of the luminescent dye is greater than or equal to the first singlet energy level (S 1 g )
- the luminescent dye is a fluoroborazine methylene bipyridine compound or a fluoroboron methylene bipyridine compound.
- the doping ratio of the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound in the organic light-emitting layer as a luminescent dye is 0.1-50wt%; the proportion of the wide bandgap material as the host material in the organic light-emitting layer is 50-99.9wt%.
- fluoroborazine methylene bipyridine compound or fluoroboromethylene bipyridine compound used as a luminescent dye has a structure shown in the following formula [1]:
- Y is C or N
- Ring A and ring A' are respectively independently represented as azine rings, and the number of carbon atoms in the azine rings is 4-12;
- R 1 and R 2 are independently represented as halogen
- R 3 and R 4 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, C1-C10 alkoxy, cyanide C6-C30 arylamino group, C3-C30 heteroarylamino group, substituted or unsubstituted C6-C60 monocyclic aryl group, C6-C60 fused-ring aryl group, C6-C60 aryloxy group, C5 - one of C60 monocyclic heteroaryl, C5-C60 condensed ring heteroaryl, trimethylsilyl, said R 3 and R 4 are independently connected to the connected azine ring to form a ring or Not connected into a ring;
- n are each independently selected from 1 to the maximum allowed integer value
- the substituents are selected from deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, cyano, C6-C30 Arylamino, C3 ⁇ C30 heteroarylamino, C6 ⁇ C60 monocyclic aryl, C6 ⁇ C60 condensed ring aryl, C6 ⁇ C60 aryloxy, C5 ⁇ C60 monocyclic heteroaryl, C5 One or a combination of at least two of ⁇ C60 fused-ring heteroaryl groups.
- fluoroborazine methylene bipyridine compound or the fluoroboromethylene bipyridine compound used as a luminescent dye has a structure as shown in formula [2]:
- X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently selected from a carbon atom or a nitrogen atom;
- n and n are independently selected from 2 to 4 integers;
- Y, R 1 , R 2 are the same as those defined in formula [1]
- the definitions of R 3 and R 4 are the same as those defined in formula [1]
- at least one R 3 can be phenyl and Ring B is fused and connected, and there may be at least one R 4 that is phenyl and is fused and connected with ring B'.
- X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently selected from carbon atoms;
- R 1 and R 2 are both fluorine atoms
- one R3 is phenyl and is fused to ring B
- one R4 is phenyl and is fused to ring B' .
- the fluoroborazine methylene bipyridine compound as a luminescent dye has a structure as shown in any one of formula (1), formula (2), formula (3) or formula (4):
- the fluoroboromethylene bipyridine compound as a luminescent dye has a structure as shown in any one of formula (5), formula (6), formula (7) or formula (8):
- formula (2), formula (3), formula (4), formula (5), formula (6), formula (7), formula (8), R 3 , R 4 Each independently selected from hydrogen, deuterium or one of the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2 -Methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethyl Hexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthy
- the fluoroborazine methylene bipyridine compound or the fluoroboromethylene bipyridine compound used as a luminescent dye is selected from any of the formulas (F-1)-(F-400) Compound:
- the host material in the light-emitting layer it is selected from carbazole derivatives, carboline derivatives, spirofluorene derivatives, fluorene derivatives, silicon-containing derivatives, phosphine-containing derivatives , at least one compound in derivatives containing sulfone groups;
- the wide bandgap material is preferably selected from but not limited to compounds shown in any of the following structures:
- the present invention also provides the application of the above-mentioned organic electroluminescent device of the present invention, and the application is an application in an organic electronic device, and the organic electronic device includes an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field Effect transistors, organic thin-film solar cells, information labels, electronic artificial skin sheets, sheet-type scanners or electronic paper.
- the present invention also protects a display device including the above-mentioned organic electroluminescent device of the present invention, and the display device includes but not limited to display elements, lighting elements, information labels, electronic artificial skin sheets or electronic paper.
- Fig. 1 is a diagram of the light emitting mechanism of the organic electroluminescent device of the present invention.
- Fig. 2 is a schematic structural view of an organic electroluminescent device prepared in an example of the present invention.
- the light emitting mechanism of the organic electroluminescent device of the present invention is as follows:
- the second triplet energy level (T 2 ) of this type of dye is quite different from the first triplet energy level (T 1 ), so the radiative transition rate (k p T2 ) from T 2 to S 0 is greater than that from T 2 to S 0
- the internal conversion rate (k IC ) of T 1 that is, the triplet state of this kind of dye has the phenomenon of anti-Kasha rule.
- the T 2 energy level of this type of dye is close to the S 1 energy level, and there is a reverse intersystem jumping process from T 2 to S 1. Therefore, singlet and triplet excitons are generated when holes and electrons recombine. All types of dyes can be utilized.
- the above-mentioned dye is matched with a wide-bandgap host, so that the dye concentration can be diluted, and the triplet-triplet annihilation (TTA) and triplet-polaron annihilation (TPA) are reduced.
- TTA triplet-triplet annihilation
- TPA triplet-polaron annihilation
- the exciton utilization rate of the dye is further improved, and the stability of the device is enhanced.
- the boron compound-doped dye with a specific structure used in the present invention does not have obvious intramolecular charge transfer, so it is beneficial to the narrowing of the spectrum and improves the color purity of the device.
- the organic electroluminescent device of the present invention includes an anode 2 , a hole transport region 3 , an organic light-emitting layer 4 , an electron transport region 5 and a cathode 6 sequentially deposited on a substrate 1 .
- the substrate can be made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency.
- a thin-film transistor (TFT) may be provided on a substrate for a display.
- the anode can be formed by sputtering or depositing the anode material on the substrate, wherein the anode material can be indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO 2 ), zinc oxide (ZnO) and other oxide transparent conductive materials and any combination thereof;
- the cathode can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg- In), magnesium-silver (Mg-Ag) and other metals or alloys and any combination thereof.
- the organic material layer of the hole transport region, the light-emitting layer, the electron transport region and the cathode can be sequentially prepared on the anode by vacuum thermal evaporation, spin coating, printing and other methods.
- the compound used as the organic material layer may be small organic molecules, organic macromolecules, polymers, and combinations thereof.
- the present invention innovates the composition of the organic light-emitting layer, specifically, the organic light-emitting layer of the present invention includes a host material and a fluoroborazamethylene bipyridine compound or a fluoroboromethylene bipyridine compound as a luminescent dye .
- the host material is a wide bandgap material, the singlet energy level (S 1 h ) of the wide bandgap material is greater than that of the doped dye (S 1 g ), and the triplet energy level (T 1 h ) of the wide bandgap material greater than the second triplet energy level (T 2 g ) of the dopant dye; the second triplet energy level (T 2 g ) of the luminescent dye is greater than the first singlet energy level (S 1 g ) of the luminescent dye.
- the host material of the present invention is a wide bandgap material, which can dilute the concentration of fluoroborazine methylene bipyridine compounds or fluoroboron methylene bipyridine compounds as luminescent dyes, effectively reducing the exciton density , so as to effectively suppress triplet-triplet annihilation (TTA) and exciton-polaron quenching (TPA), further enhance the stability of organic electroluminescent devices, improve device life, and reduce efficiency roll-off.
- TTA triplet-triplet annihilation
- TPA exciton-polaron quenching
- the difference between the HOMO energy level and the LUMO energy level of the wide bandgap material of the present invention is greater than or equal to 2eV, thereby ensuring that the singlet state and triplet state of the wide bandgap material are at a higher energy level, which is beneficial to the wide bandgap material to the luminescent dye of the present invention.
- the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound used as a luminescent dye in the present invention has a planar aromatic rigid structure and a stable structure. Its second triplet energy level (T 2 ) is quite different from the first triplet energy level (T 1 ), so the radiative transition rate (k p T2 ) from T 2 to S 0 is greater than that from T 2 to T 1
- the internal conversion rate (k IC ) that is, the triplet state of such dyes has the phenomenon of anti-Kasha rule.
- the T 2 energy level of this type of dye is close to the S 1 energy level, and there is a reverse intersystem crossing process from T 2 to S 1. Therefore, singlet and triplet excitons are generated when holes and electrons recombine. All types of dyes can be utilized.
- the first singlet energy level of the host material wide bandgap material is greater than the first singlet energy level of the boron compound dye, and the first singlet energy level of the host material wide bandgap material is greater than the second singlet energy level of the luminescent dye.
- the first triplet energy level of the host material wide bandgap material is greater than the second triplet energy level of the luminescent dye, therefore, after the organic electroluminescent device is electrically excited, the singlet energy level of the wide bandgap host
- Both the heavy state and the triplet excitonic energy can be transferred to the singlet state and triplet state of the dye material respectively; or the holes and electrons are directly recombined on the dye, which is realized through the reverse intersystem crossing process of the dye T 2 to S 1 High-efficiency light emission, and finally the singlet and triplet energy in the organic electroluminescent device has been fully utilized, which improves the luminous efficiency of the organic electroluminescent device; therefore, the present invention can effectively reduce the concentration of triplet excitons, thereby solving the problem of The problem of serious roll-off decline under high brightness effectively enhances the stability of the organic electroluminescent device.
- the first triplet energy level (T 1 h ) of the host material wide bandgap material is at least 0.1eV higher than the second triplet energy level (T 2 g ) of the luminescent dye, that is, T 1 h -T 2 g >0.1eV;
- the first singlet energy level (S 1 g ) of the luminescent dye is at least 0.3eV higher than the first triplet energy level (T 1 g ), that is, S 1 g -T 1 g >0.3eV;
- the second triplet energy level (T 2 g ) of the compound dye is at least 0.3eV higher than the first triplet energy level (T 1 g ), ie T 2 g -T 1 g >0.3eV;
- the present invention innovates the composition of the organic light-emitting layer, and uses a wide-bandgap host to match such a fluoroborazamethylene bipyridine compound or a fluoroboromethylene bipyridine compound as a luminescent dye, which can not only improve the organic light emission
- a fluoroborazamethylene bipyridine compound or a fluoroboromethylene bipyridine compound as a luminescent dye
- the proportion of the wide bandgap material in the organic light-emitting layer is 50wt%-99.9wt%; the proportion of the luminescent dye in the organic light-emitting layer is 0.1wt%-50wt%.
- the stability of the device is higher and the lifetime is gradually extended.
- An organic electroluminescent device includes an anode, a cathode, and a layer of organic material between the two electrodes.
- the organic material can be divided into multiple regions.
- the organic material layer can include a hole transport region, a light emitting layer, and an electron transport region.
- the material of the anode can be oxide transparent conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO) and any combination thereof.
- the cathode material can be magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag ) and other metals or alloys and any combination of them.
- the hole transport region is located between the anode and the light emitting layer.
- the hole transport region can be a hole transport layer (HTL) with a single-layer structure, including a single-layer hole-transport layer containing only one compound and a single-layer hole-transport layer containing multiple compounds.
- the hole transport region may also be a multilayer structure including at least one layer of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL).
- HIL hole injection layer
- HTL hole transport layer
- EBL electron blocking layer
- the material of the hole transport region can be selected from but not limited to phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly(4 - Styrene sulfonate) (Pani/PSS), aromatic amine derivatives, etc.
- phthalocyanine derivatives such as CuPc
- conductive polymers or polymers containing conductive dopants such as polyphenylene vinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/ DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-
- the luminescent layer includes luminescent dyes (that is, dopant) that can emit different wavelength spectra, and can also include a host material (Host) at the same time.
- the light-emitting layer may be a monochromatic light-emitting layer that emits a single color such as red, green, or blue.
- a plurality of monochromatic light-emitting layers of different colors can be arranged planarly according to the pixel pattern, and can also be stacked together to form a colored light-emitting layer. When the light-emitting layers of different colors are stacked together, they can be separated from each other or connected to each other.
- the light-emitting layer can also be a single color light-emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
- the electron transport region may be a single-layer electron transport layer (ETL), including a single-layer electron-transport layer containing only one compound and a single-layer electron-transport layer containing multiple compounds.
- the electron transport region may also be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).
- EIL electron injection layer
- ETL electron transport layer
- HBL hole blocking layer
- the present invention also provides a preparation method of the organic electroluminescent device, which is illustrated by taking FIG. 1 as an example, including sequentially depositing an anode 2, a hole transport region 3, an organic light-emitting layer 4, an electron transport region 5, and a cathode 6 on a substrate 1, Then package.
- the organic light-emitting layer 4 is formed by co-evaporating a wide bandgap material source, an electron donor material source, an electron acceptor material source and a resonant TADF material source.
- the preparation method of the organic electroluminescent device of the present invention comprises the following steps:
- the light-emitting layer includes the host material and TADF dye.
- the evaporation rate of the host material and the evaporation rate of the sensitizer material are adjusted by the method of multi-source co-evaporation. and the evaporation rate of the dye to make the dye reach the preset doping ratio;
- the electron transport layer material of the device is vacuum evaporated on the organic light-emitting layer, and the evaporation rate is 0.1-0.5nm/s;
- An embodiment of the present invention also provides a display device, which includes the organic electroluminescent device as provided above.
- the display device may be a display device such as an OLED display, and any product or component having a display function such as a TV, a digital camera, a mobile phone, a tablet computer, etc. including the display device.
- the display device has the same advantages as that of the above-mentioned organic electroluminescent device over the prior art, which will not be repeated here.
- the organic electroluminescence device of the present invention will be further introduced through specific examples below.
- the OLED includes sequentially stacked anode/hole injection layer/hole transport layer/first exciton blocking layer/light emitting layer/second exciton blocking layer/electron transport layer/electron injection layer /cathode.
- the anode is ITO; the hole injection layer is HATCN; the hole transport layer is NPB; the electron transport layer is DPyPA and Liq co-evaporation; the electron injection layer is LiF; the cathode is Al.
- the glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone: ethanol mixed solvent, baked in a clean environment until the water is completely removed, and then cleaned with ultraviolet light. Light and ozone cleaning, and bombardment of the surface with a beam of low-energy cations;
- HATCN was vacuum evaporated on the ITO transparent conductive layer as the hole injection layer of the device, the evaporation rate was 0.1nm/s, and the total film thickness was 5nm;
- NPB hole transport layer of the device
- the evaporation rate was 0.1nm/s
- the total film thickness was 30nm
- the light-emitting layer of the device is vacuum-evaporated on the hole-transporting layer, and the light-emitting layer of the present invention includes a host material and a dye material. Adjust the evaporation rate of the main material to 0.1nm/s, adjust the evaporation rate of the dye in the luminescent layer to be 1% of the evaporation rate of the main body, and set the total film thickness of the luminescent layer to 30nm;
- the co-evaporation ratio is 1:1, the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 30nm;
- LiF with a thickness of 0.5 nm was vacuum evaporated on the electron transport layer as the electron injection layer, and an Al layer with a thickness of 150 nm was used as the cathode of the device.
- the first triplet energy level of the host material, the first singlet state and the second triplet energy level of the boron compound dye are shown in Table 1.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dye concentration of the organic light-emitting layer is different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 1, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Embodiment 1, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 2, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 3, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Embodiment 4, the only difference being that the type of the main body is different.
- the significance of the device is roughly the same as that of Embodiment 5, the only difference being that the type of the main body is different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the meaning of the device is roughly the same as that of Example 2, the only difference is that the dyes in the organic light-emitting layer are different.
- the device structure of this comparison example is as follows:
- the meaning of the device of this comparative example is roughly the same as that of Example 1, the only difference is that the main body of the organic light-emitting layer and the type of dye are different.
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the device structure of this comparison example is as follows:
- the organic electroluminescent device (embodiment 1-100, comparative example 1-10) prepared by the above-mentioned process is subjected to following performance measurement: the characteristics such as the current, voltage, luminance, luminescence spectrum, current efficiency, external quantum efficiency of the prepared device Adopt PR 655 spectral scanning luminance meter and Keithley K2400 digital source meter system to test synchronously.
- Turn-on voltage increase the voltage at a rate of 0.1V per second, and measure the voltage when the brightness of the organic electroluminescent device reaches 1cd/m2, which is the turn - on voltage;
- this type of organic electroluminescent device of the present invention adopts a brand-new combination scheme of host materials and dyes, and the devices prepared thereby have excellent photoelectric properties, and the electroluminescence external quantum efficiencies of all devices All are above 12%, showing overall superiority.
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Abstract
Description
Claims (13)
- 一种有机电致发光器件,包括第一电极、第二电极和有机功能层,所述有机功能层中包括有机发光层,所述有机发光层中包括主体材料和发光染料,其特征在于,所述主体材料为宽带隙材料,该主体材料的单重态能级(S 1 h)大于发光染料的第一单重态能级(S 1 g),并且所述主体材料的三重态能级(T 1 h)大于或等于发光染料的第二三重态能级(T 2 g); An organic electroluminescent device, comprising a first electrode, a second electrode and an organic functional layer, the organic functional layer includes an organic light-emitting layer, and the organic light-emitting layer includes a host material and a luminescent dye, characterized in that the The host material is a wide bandgap material, the singlet energy level (S 1 h ) of the host material is greater than the first singlet energy level (S 1 g ) of the luminescent dye, and the triplet energy level ( T 1 h ) is greater than or equal to the second triplet energy level (T 2 g ) of the luminescent dye;所述发光染料的第二三重态能级(T 2 g)大于或等于发光染料的第一单重态能级(S 1 g); The second triplet energy level (T 2 g ) of the luminescent dye is greater than or equal to the first singlet energy level (S 1 g ) of the luminescent dye;所述发光染料为氟硼氮杂亚甲基联吡啶类化合物或氟硼亚甲基联吡啶类化合物。The luminescent dye is a fluoroborazine methylene bipyridine compound or a fluoroboron methylene bipyridine compound.
- 根据权利要求1所述的有机电致发光器件,其特征在于,所述作为发光染料的氟硼氮杂亚甲基联吡啶类化合物或氟硼亚甲基联吡啶类化合物在所述有机发光层中的掺杂比例为0.1-50wt%;The organic electroluminescent device according to claim 1, wherein the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound as the luminescent dye is in the organic light-emitting layer The doping ratio in is 0.1-50wt%;所述作为主体材料的宽带隙材料在所述有机发光层中的比例为50-99.9wt%。The proportion of the wide bandgap material as the host material in the organic light-emitting layer is 50-99.9wt%.
- 根据权利要求1所述的有机电致发光器件,其特征在于,所述作为发光染料的氟硼氮杂亚甲基联吡啶类化合物或氟硼亚甲基联吡啶类化合物具有如下式[1]所示的结构:The organic electroluminescent device according to claim 1, wherein the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound as a luminescent dye has the following formula [1] The structure shown:式[1]中,Y为N或C;In formula [1], Y is N or C;环A和环A’分别独立地表示为吖嗪环,所述吖嗪环中的碳原子数为4-12个;Ring A and ring A' are respectively independently represented as azine rings, and the number of carbon atoms in the azine rings is 4-12;R 1、R 2分别独立地表示为卤素; R 1 and R 2 are independently represented as halogen;R 3、R 4分别独立地选自氢、氘、取代或未取代的C1~C36的链状烷基、取代或未取代的C3~C36的环烷基、C1~C10的烷氧基、氰基、C6~C30的芳基氨基、C3~C30杂芳基氨基、取代或未取代的C6-C60的单环芳基、C6-C60的稠环芳基、C6-C60的芳氧基、C5-C60的单环杂芳基、C5-C60的稠环杂芳基、三甲基硅基中的一种,所述R 3、R 4分别独立地与相连接的吖嗪环连接成环或不连接成环; R 3 and R 4 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, C1-C10 alkoxy, cyanide C6-C30 arylamino group, C3-C30 heteroarylamino group, substituted or unsubstituted C6-C60 monocyclic aryl group, C6-C60 fused-ring aryl group, C6-C60 aryloxy group, C5 - one of C60 monocyclic heteroaryl, C5-C60 condensed ring heteroaryl, trimethylsilyl, said R 3 and R 4 are independently connected to the connected azine ring to form a ring or Not connected into a ring;m和n分别独立地选自1至最大允许的整数值;m and n are each independently selected from 1 to the maximum allowed integer value;当上述基团存在取代基时,所述取代基选自氘、卤素、C1~C30的链状烷基、C3~C30的环烷基、C1~C10的烷氧基、氰基、C6~C30的芳基氨基、C3~C30杂芳基氨基、C6~C60的单环芳基、C6~C60的稠环芳基、C6~C60的芳氧基、C5~C60的单环杂芳基、C5~C60的稠环杂芳基中的一种或者至少两种的组合。When the above-mentioned groups have substituents, the substituents are selected from deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, cyano, C6-C30 Arylamino, C3~C30 heteroarylamino, C6~C60 monocyclic aryl, C6~C60 condensed ring aryl, C6~C60 aryloxy, C5~C60 monocyclic heteroaryl, C5 One or a combination of at least two of ~C60 fused-ring heteroaryl groups.
- 根据权利要求1所述的有机电致发光器件,其特征在于,所述作为发光染料的氟硼氮杂亚甲基联吡啶类化合物或氟硼亚甲基联吡啶类化合物具有如式[2]所示的结构:The organic electroluminescent device according to claim 1, wherein the fluoroborazamethylene bipyridine compound or the fluoroborazamethylene bipyridine compound as a luminescent dye has the formula [2] The structure shown:式[2]中,X 1、X 2、X 3、X 4、X 5、X 6、X 7、X 8分别独立地选自碳原子或氮原子; In formula [2], X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are each independently selected from a carbon atom or a nitrogen atom;m和n分别独立地选自2~4的整数;m and n are independently selected from 2 to 4 integers;Y为N或C;Y is N or C;R 1、R 2分别独立地表示为卤素; R 1 and R 2 are independently represented as halogen;R 3、R 4分别独立地选自氢、氘、取代或未取代的C1~C36的链状烷基、取代或未取代的C3~C36的环烷基、C1~C10的烷氧基、氰基、C6~C30的芳基氨基、C3~C30杂芳基氨基、取代或未取代的C6-C60的单环芳基、C6-C60的稠环芳基、C6-C60的芳氧基、C5-C60的单环杂芳基、C5-C60的稠环杂芳基、三甲基硅基中的一种,所述R 3、R 4分别独立地与相连接的吖嗪环连接成环或不连接成环; R 3 and R 4 are independently selected from hydrogen, deuterium, substituted or unsubstituted C1-C36 chain alkyl, substituted or unsubstituted C3-C36 cycloalkyl, C1-C10 alkoxy, cyanide C6-C30 arylamino group, C3-C30 heteroarylamino group, substituted or unsubstituted C6-C60 monocyclic aryl group, C6-C60 fused-ring aryl group, C6-C60 aryloxy group, C5 - one of C60 monocyclic heteroaryl, C5-C60 condensed ring heteroaryl, trimethylsilyl, said R 3 and R 4 are independently connected to the connected azine ring to form a ring or Not connected into a ring;当上述基团存在取代基时,所述取代基选自氘、卤素、C1~C30的链状烷基、C3~C30的环烷基、C1~C10的烷氧基、氰基、C6~C30的芳基氨基、C3~C30杂芳基氨基、C6~C60的单环芳基、C6~C60的稠环芳基、C6~C60的芳氧基、C5~C60的单环杂芳基、C5~C60的稠环杂芳基中的一种或者至少两种的组合。When the above-mentioned groups have substituents, the substituents are selected from deuterium, halogen, C1-C30 chain alkyl, C3-C30 cycloalkyl, C1-C10 alkoxy, cyano, C6-C30 Arylamino, C3~C30 heteroarylamino, C6~C60 monocyclic aryl, C6~C60 condensed ring aryl, C6~C60 aryloxy, C5~C60 monocyclic heteroaryl, C5 One or a combination of at least two of ~C60 fused-ring heteroaryl groups.
- 根据权利要求4所述的有机电致发光器件,其特征在于,式[2]中,有至少一个R 3为苯基并与环B稠合连接; The organic electroluminescent device according to claim 4, characterized in that, in formula [2], at least one R is phenyl and is fused and connected with ring B;和/或,有至少一个R 4为苯基并与环B’稠合连接。 And/or, at least one R4 is phenyl and is fused to ring B' .
- 根据权利要求4所述的有机电致发光器件,其特征在于,式[2]中,X 1、X 2、X 3、X 4、X 5、X 6、X 7、X 8分别独立地选自碳原子; The organic electroluminescent device according to claim 4, characterized in that, in formula [2], X 1 , X 2 , X 3 , X 4 , X 5 , X 6 , X 7 , and X 8 are independently selected from from carbon atoms;和/或,R 1、R 2均为氟原子; And/or, R 1 and R 2 are both fluorine atoms;和/或,有一个R 3为苯基并与环B稠合连接,有一个R 4为苯基并与环B’稠合连接。 And/or, one R3 is phenyl and is fused to ring B, and one R4 is phenyl and is fused to ring B' .
- 根据权利要求3或4所述的有机电致发光器件,其特征在于,所述作为发光染料的氟硼氮杂亚甲基联吡啶类化合物具有如式(1)、式(2)、式(3)或式(4)中任一所示的结构:The organic electroluminescent device according to claim 3 or 4, characterized in that, the fluoroborazine methylene bipyridine compound as the luminescent dye has formula (1), formula (2), formula ( 3) or any structure shown in formula (4):式(1)、式(2)、式(3)、式(4)中,m、n、R 1、R 2、R 3、R 4的定义与在式[1]中的定义相同; In formula (1), formula (2), formula (3), and formula (4), the definitions of m, n, R 1 , R 2 , R 3 , and R 4 are the same as those in formula [1];所述作为发光染料的氟硼亚甲基联吡啶类化合物具有如式(5)、式(6)、式(7)或式(8)中任一所示的结构:The fluoroboromethylene bipyridine compound as a luminescent dye has a structure as shown in any one of formula (5), formula (6), formula (7) or formula (8):式(5)、式(6)、式(7)、式(8)中,m、n、R 1、R 2、R 3、R 4的定义与在式[1]中的定义相同。 In Formula (5), Formula (6), Formula (7), and Formula (8), the definitions of m, n, R 1 , R 2 , R 3 , and R 4 are the same as those in Formula [1].
- 根据权利要求7所述的有机电致发光器件,其特征在于,式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)、式(8)中:The organic electroluminescent device according to claim 7, characterized in that, formula (1), formula (2), formula (3), formula (4), formula (5), formula (6), formula (7) ), formula (8):R 3、R 4分别独立地选自氢、氘或者下述取代基团中的一种:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、 三氟甲基、五氟乙基、2,2,2-三氟乙基、苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、窟基、茈基、荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、三聚苯基、四联苯基、芴基、螺二芴基、二氢菲基、二氢芘基、四氢芘基、顺式或反式茚并芴基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、三氟甲基苯基、甲氧基苯基、二甲氧基苯基、三甲氧基苯基、二三氟甲基苯基、咔唑基苯基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、异吲哚基、咔唑基、茚并咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并-5,6-喹啉基、苯并-6,7-喹啉基、苯并-7,8-喹啉基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、嗯唑基、苯并嗯唑基、萘并嗯唑基、蒽并嗯唑基、菲并嗯唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂茈基、吡嗪基、吩嗪基、吩噻嗪基、萘啶基、氮杂咔唑基、苯并咔啉基、菲咯啉基、1,2,3-三唑基、1,2,4-三唑基、苯并三唑基、1,2,3-噁二唑基、1,2,4-嗯二唑基、1,2,5_嗯二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、苯并噻二唑基、9,9-二甲基吖啶基、二芳胺基、金刚烷基、氟代苯基、甲基苯基、三甲基苯基、氰基苯基、四氢吡咯、哌啶、甲氧基、三甲基硅基,或者选自以上两种取代基团的组合; R 3 and R 4 are independently selected from hydrogen, deuterium or one of the following substituent groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl Base, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, trifluoroethyl , pyrenyl, pyrenyl, perylene, fluoranthene, tetraphenyl, pentaphenyl, benzopyrenyl, biphenyl, diphenyl, terphenyl, triphenyl, quaternyl , fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, triindenyl, isotriindenyl, spirotriindenyl , spiroisotriindenyl, trifluoromethylphenyl, methoxyphenyl, dimethoxyphenyl, trimethoxyphenyl, ditrifluoromethylphenyl, carbazolylphenyl, furyl , Benzofuryl, Isobenzofuryl, Dibenzofuryl, Thienyl, Benzothienyl, Isobenzothienyl, Dibenzothienyl, Pyrrolyl, Isoindolyl, Carbazolyl, Indenocarbazolyl, pyridyl, quinolinyl, isoquinolyl, acridinyl, phenanthridyl, benzo-5,6-quinolyl, benzo-6,7-quinolyl, benzo -7,8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthimidazolyl, phenanthroimidazolyl, pyridimidazolyl, pyrazinoimidazolyl, quinoxalino Imidazolyl, oxazolyl, benzoxazolyl, naphthiazolyl, anthrazolyl, phenanthrazolyl, 1,2-thiazolyl, 1,3-thiazolyl, benzothiazolyl, Pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1,5-diazaanthracenyl, 2,7-diazapyrenyl, 2,3-diazapyrenyl Pyrenyl, 1,6-diazapyrenyl, 1,8-diazapyrenyl, 4,5-diazapyrenyl, 4,5,9,10-tetraazapyrenyl, pyrazinyl , phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbolinyl, phenanthrolinyl, 1,2,3-triazolyl, 1,2,4-triazolyl , Benzotriazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl , 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, 1,3,5-triazinyl, 1,2,4- Triazinyl, 1,2,3-triazinyl, tetrazolyl, 1,2,4,5-tetrazinyl, 1,2,3,4-tetrazinyl, 1,2,3,5- Tetrazine, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9,9-dimethylacridinyl, diarylamine, adamantyl, fluorophenyl, methylbenzene Base, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, trimethylsilyl, or a combination of the above two substituent groups;和/或,R 1、R 2均为氟原子。 And/or, both R 1 and R 2 are fluorine atoms.
- 根据权利要求3或4所述的有机电致发光器件,其特征在于,作为发光染料的氟硼氮杂亚甲基联吡啶类化合物或氟硼亚甲基联吡啶类化合物,选自式(F-1)-(F-400)中任一所示的化合物:The organic electroluminescent device according to claim 3 or 4, wherein the fluoroborazine methylene bipyridine compound or the fluoroboron methylene bipyridine compound as a luminescent dye is selected from the group consisting of formula (F Any one of the compounds shown in -1)-(F-400):
- 根据权利要求1所述的有机电致发光器件,其特征在于,作为发光层中主体材料的所述宽带隙材料选自咔唑类衍生物、咔啉类衍生物、螺芴类衍生物、芴类衍生物、含硅基类衍生物、含膦氧基类衍生物、含砜基类衍生物中的至少一种化合物。The organic electroluminescent device according to claim 1, wherein the wide bandgap material used as the host material in the light-emitting layer is selected from the group consisting of carbazole derivatives, carboline derivatives, spirofluorene derivatives, fluorene At least one compound among derivatives, silicon-containing derivatives, phosphine-containing derivatives, and sulfone-containing derivatives.
- 一种根据权利要求1所述的有机电致发光器件的应用,其特征在于,所述应用为在有机电子装置中的应用,所述有机电子装置包括光学传感器、太阳能电池、照明元件、有机薄膜晶体管、有机场效应晶体管、信息标签、电子人工皮肤片材、片材型扫描器或电子纸。An application of the organic electroluminescent device according to claim 1, wherein the application is an application in an organic electronic device, and the organic electronic device includes an optical sensor, a solar cell, a lighting element, an organic thin film Transistors, organic field effect transistors, information labels, electronic artificial skin sheets, sheet-type scanners or electronic paper.
- 一种显示装置,其特征在于,包括权利要求1所述的有机电致发光器件,所述显示装置为显示元件、照明元件、信息标签、电子人工皮肤片材或电子纸。A display device, characterized in that it comprises the organic electroluminescent device according to claim 1, and the display device is a display element, a lighting element, an information label, an electronic artificial skin sheet or electronic paper.
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CN107507921A (en) * | 2017-09-29 | 2017-12-22 | 江苏三月光电科技有限公司 | A kind of boracic organic electroluminescence device and preparation method thereof |
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