WO2024021988A1 - Complexe organométallique, formulation, dispositif optoélectronique organique et appareil d'affichage ou d'éclairage - Google Patents

Complexe organométallique, formulation, dispositif optoélectronique organique et appareil d'affichage ou d'éclairage Download PDF

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WO2024021988A1
WO2024021988A1 PCT/CN2023/103790 CN2023103790W WO2024021988A1 WO 2024021988 A1 WO2024021988 A1 WO 2024021988A1 CN 2023103790 W CN2023103790 W CN 2023103790W WO 2024021988 A1 WO2024021988 A1 WO 2024021988A1
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substituted
group
unsubstituted
organic
layer
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PCT/CN2023/103790
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Chinese (zh)
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赵晓宇
申屠晓波
张磊
吴空物
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宇瑞(上海)化学有限公司
浙江华显光电科技有限公司
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Publication of WO2024021988A1 publication Critical patent/WO2024021988A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006—Palladium compounds

Definitions

  • the present invention relates to an organic metal complex, in particular to an organic metal complex, a preparation, an organic optoelectronic device and a display or lighting device, and belongs to the field of organic optoelectronics.
  • Organic optoelectronic devices especially organic electroluminescent diodes (OLED) have the characteristics of self-illumination, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, fast response speed, wide applicable temperature range, low driving voltage, and can be manufactured in flexible and The unique advantages of curved and transparent display panels and environmental friendliness can be applied to flat panel displays and new generation lighting, and can also be used as backlight sources for LCDs.
  • OLED organic electroluminescent diodes
  • OLED Since its invention in the late 1980s, OLED has been used in industry. OLED emits light in two ways: fluorescence and phosphorescence. According to theoretical speculation, the difference between the singlet excited state and the triplet excited state generated by carrier recombination The ratio is 1:3, so when using small molecule fluorescent materials, only 25% of the total energy can be used to emit light, and the remaining 75% of the energy is lost due to the non-luminescent mechanism of the triplet excited state, so it is generally considered that fluorescent materials The internal quantum efficiency limit is 25%. In 1998, Professor Forrest and others discovered that triplet phosphorescence could be utilized at room temperature, and raised the upper limit of the original internal quantum efficiency to 100%.
  • Triplet phosphors are often complexes composed of heavy metal atoms, and use the heavy atom effect to strongly
  • the spin-orbit coupling effect causes the originally forbidden triplet energy to emit light in the form of phosphorescence, and the quantum efficiency is also greatly improved.
  • the luminescent layers in organic OLED components almost all use the host-guest luminescent system mechanism, that is, the host material is doped with the guest luminescent material.
  • the energy system of the organic host material is larger than that of the guest material, that is, the energy is transferred from the host to the guest material.
  • the object causes the object material to be excited and emit light.
  • Commonly used phosphorescent organic host materials have high triplet energy levels. When the organic host material is excited by an electric field, the triplet energy can be effectively transferred from the organic host material to the guest phosphorescent material.
  • Commonly used organic guest materials are iridium and platinum metal compounds. However, there are still some technical difficulties in the development of platinum and palladium complex materials and devices. For example, OLED requires high efficiency, long life, and lower operating voltage.
  • the object of the present invention is to provide a novel organic metal complex and an organic optoelectronic device (especially an organic electroluminescent diode) containing the same.
  • Applying the organic metal complex of the present invention to an organic optoelectronic device can improve the current efficiency of the device, reduce the operating voltage of the device, and extend the life of the device.
  • the invention provides an organic metal complex, the structure of which is shown in Formula I:
  • M is selected from platinum or palladium
  • R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aromatic group group, C6 to C40 heteroaryl group, C6 to C60 substituted or unsubstituted heterospirocyclic ring, C6 to C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, Substituted
  • n is an integer from 0 to 10;
  • n is an integer from 0 to 4.
  • the coordination group on the pyridine side is selected from any one of the following structures:
  • R is hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aryl group , C6 ⁇ C40 heteroaryl group, C6 ⁇ C60 substituted or unsubstituted heterospirocyclic ring, C6 ⁇ C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or un unsub
  • n is an integer from 0 to 10;
  • n is an integer from 0 to 4.
  • R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl.
  • formula (I) is selected from any one of the following structures:
  • the present invention also provides a preparation comprising the organometallic complex and at least one solvent, wherein the solvent is an unsaturated hydrocarbon solvent, a saturated hydrocarbon solvent, an ether solvent or an ester solvent.
  • the invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer.
  • the organic layer is a hole injection layer, a hole transport layer, a light-emitting layer (active layer), a hole blocking layer, an electron layer, and a hole injection layer. At least one of an injection layer or an electron transport layer, wherein the organic layer contains the organic metal complex.
  • the organic layer is a light-emitting layer
  • the light-emitting layer contains the organic metal complex and the corresponding host material, wherein the mass percentage of the organic metal complex is between 1% and 50%, and the host material has no limit.
  • the organic optoelectronic device is an organic photovoltaic device, an organic light-emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC), an organic thin film transistor (OTFT) or an organic Memory device (Organic Memory Element).
  • OLED organic light-emitting device
  • OSC organic solar cell
  • e-paper electronic paper
  • OPC organic photoreceptor
  • OFT organic thin film transistor
  • OFT organic thin film transistor
  • Organic Memory Element Organic Memory Element
  • the invention also provides an organic optoelectronic device, which includes a cathode layer, an anode layer and an organic layer.
  • the organic layer is a light-emitting layer, wherein the light-emitting layer contains an organic metal complex, and the structure of the organic metal complex is as follows Formula I shows:
  • M is selected from platinum or palladium
  • R 1 , R 2 , R 3 and R are each independently selected from hydrogen, deuterium, halogen, hydroxyl, cyano, nitro, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group Or its salt, phosphate group or its salt, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aromatic group Base, C6 ⁇ C40 heteroaryl group, C6 ⁇ C60 substituted or unsubstituted heterospirocyclic ring, C6 ⁇ C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group ether group, substituted or unsubstituted arylamine group, substituted or unsub
  • n is an integer from 0 to 10;
  • n is an integer from 0 to 4.
  • the coordination group on the pyridine side is selected from any one of the following structures:
  • R is hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl group, C1 ⁇ C18 alkoxy group, C1 ⁇ C18 alkylsilyl group, C1 ⁇ C18 alkoxysilyl group, C6 ⁇ C40 substituted or unsubstituted aryl group , C6 ⁇ C40 heteroaryl group, C6 ⁇ C60 substituted or unsubstituted heterospirocyclic ring, C6 ⁇ C60 substituted or unsubstituted spirocyclic ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl group Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or un unsub
  • n is an integer from 0 to 10;
  • n is an integer from 0 to 4.
  • R 1 , R 2 , R 3 and R are each independently selected from hydrogen, methyl, ethyl, tert-butyl or tert-butylbiphenyl.
  • the present invention further provides a display or lighting device including the organic optoelectronic device.
  • the spiro ring-containing organometallic complex of the present invention has good thermal stability. By introducing a rigid spirocyclic structure into the organometallic complex and increasing steric hindrance, the interaction between planar Pt complex molecules can be effectively suppressed, thereby improving device efficiency.
  • the spiro ring-containing organometallic complex of the present invention has good electron and hole receiving capabilities, and can improve the energy transmission between the host and the guest.
  • the specific performance is as follows:
  • the invented spiro ring-containing organometallic complex is used as a functional layer (organic layer), especially as an organic optoelectronic device produced as a light-emitting layer. Its current efficiency is increased, the lighting voltage is reduced, and the life of the device is greatly improved, indicating that most After the electrons and holes recombine, the energy is effectively transferred to the organometallic complex to emit light instead of heat.
  • Figure 1 is a schematic structural diagram of an organic optoelectronic device of the present invention, in which 110 represents the substrate, 120 represents the anode, 130 represents the hole injection layer, 140 represents the hole transport layer, 150 represents the light-emitting layer, 160 represents the hole blocking layer, 170 Indicates the electron transport layer, 180 indicates the electron injection layer, and 190 indicates the cathode.
  • permissible substituents include cyclic and acyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds.
  • exemplary substituents include those described below.
  • the permissible substituents may be one or more, the same or different.
  • a heteroatom eg, nitrogen
  • the present invention is not intended to be limited in any way by the permissible substituents of organic compounds.
  • substituted or “substituted with” includes the implicit proviso that such substitution is consistent with the permissible valence bonds of the substituting atom and the substituent, and that the substitution results in a stable compound (e.g., one that does not spontaneously undergo transformation) For example, compounds by rearrangement, cyclization, elimination, etc.).
  • individual substituents can be further optionally substituted (ie, further substituted or unsubstituted) unless expressly stated to the contrary.
  • R1", R2”, R3", “R4", “R5" and “R” are used as general symbols in the present invention to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed in the present invention, and when they are defined as certain substituents in one example, they can also be defined as some other substituents in another example.
  • alkyl used in the present invention refers to a branched or unbranched saturated hydrocarbon group of 1 to 18 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl Alkyl, eicosyl, tetradecyl, etc.
  • the alkyl group may be cyclic or acyclic.
  • the alkyl group may be branched or unbranched.
  • the alkyl group may also be substituted or unsubstituted.
  • the alkyl group can substitute one or more groups, including but not limited to optionally substituted alkyl, cycloalkyl, alkoxy, amino, ether, halogen, hydroxyl, nitro, methyl as described in the present invention.
  • a "lower alkyl” group is an alkyl group containing 1 to 6 (eg, 1 to 4) carbon atoms.
  • alkyl generally refers to both unsubstituted and substituted alkyl groups; however, substituted alkyl groups are also specifically referred to herein by identifying the specific substituents on the alkyl group.
  • halogenated alkyl or “haloalkyl” specifically refers to an alkyl group substituted with one or more halogens (eg, fluorine, chlorine, bromine, or iodine).
  • alkoxyalkyl specifically refers to an alkyl group substituted with one or more alkoxy groups, as described below.
  • alkylamino specifically refers to an alkyl group substituted with one or more amino groups, as described below, etc.
  • alkyl is used in one context and a specific term such as “alkyl alcohol” is used in another context, it is not meant to imply that the term “alkyl” does not also refer to a specific term such as “alkyl” Alcohol” etc.
  • aryl as used herein is a substituted or unsubstituted phenyl group of 6 to 60 carbon atoms, such as methylphenyl, ethylphenyl, n-propylphenyl, isopropylphenyl, n-butyl phenyl, isobutylphenyl, sec-butylphenyl, tert-butylphenyl, tert-butylbiphenyl, n-pentylphenyl, isopentylphenyl, sec-pentylphenyl, neopentyl Phenyl, hexylphenyl, heptylphenyl, octylphenyl, nonylphenyl, decylphenyl, dodecylphenyl, tetradecylphenyl, hexadecylphenyl, eicosanyl Alkylphenyl,
  • alkoxy and “alkoxy group” as used herein refer to an alkyl or cycloalkyl group of 1 to 18 carbon atoms bonded through ether bonds; that is, “alkoxy” may be defined as— OR1, where R1 is alkyl or cycloalkyl as defined above.
  • Alkoxy also includes the alkoxy polymers just described; i.e., the alkoxy group may be a polyether, such as -OR1-OR2 or -OR1-(OR2)a-OR3, where "a” is an integer from 1 to 500 , and R1, R2 and R3 are each independently an alkyl group, a cycloalkyl group or a combination thereof.
  • aryl used in the present invention refers to any carbon-based aromatic group with 60 carbon atoms or less, including but not limited to benzene, naphthalene, phenyl, biphenyl, phenoxybenzene, etc.
  • aryl also includes "heteroaryl” which is defined as an aromatic-containing group that The ring contains at least one heteroatom. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, or phosphorus.
  • non-heteroaryl (which is also included in the term “aryl”) defines an aromatic-containing group that does not contain heteroatoms.
  • Aryl groups may be substituted or unsubstituted.
  • the aryl group may be substituted with one or more groups, including but not limited to alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, Aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halogen, hydroxyl, ketone, azido, nitro, silyl, thio-oxo group or mercapto group.
  • bias is a specific type of aryl group and is included in the definition of "aryl”. Biaryl refers to two aryl groups joined together by a fused ring structure, as in naphthalene, or by one or more carbon-carbon bonds, as in biphenyl.
  • amine or “amino” used in the present invention is represented by the formula -NR1R2, wherein R1 and R2 can be independently selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aromatic Choose from base or heteroaryl.
  • carboxylic acid as used herein is represented by the formula -C(O)OH.
  • ether used in the present invention is represented by the formula R1OR2, wherein R1 and R2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or Heteroaryl.
  • polyether used in the present invention is represented by the formula - (R1O-R2O)a-, wherein R1 and R2 can independently be alkyl, cycloalkyl, alkenyl, cycloalkenyl or alkynyl as described in the present invention. , cycloalkynyl, aryl or heteroaryl and "a" is an integer from 1 to 500.
  • halogen refers to the halogens fluorine, chlorine, bromine and iodine.
  • heterocyclic group refers to monocyclic and polycyclic non-aromatic ring systems
  • heteroaryl refers to monocyclic and polycyclic non-aromatic ring systems of not more than 60 carbon atoms.
  • the term includes azetidinyl, dioxanyl, furyl, imidazolyl, isothiazolyl, isoxazolyl, morpholinyl, oxazolyl (including 1,2,3-oxadiazolyl, 1,2,5-oxadiazolyl and 1,3,4-oxadiazolyl (oxazolyl), piperazinyl, piperidinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, Pyrimidinyl, pyrrolyl, pyrrolidinyl, tetrahydrofuryl, tetrahydropyranyl, tetrazinyl including 1,2,4,5-tetrazinyl, including 1,2,3,4-tetrazolyl and 1 , 2,4,5-tetrazolyl tetrazolyl, including 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl and 1,3,4-thiadia
  • hydroxyl as used herein is represented by the formula -OH.
  • nitro as used herein is represented by the formula -NO2.
  • nitrile as used herein is represented by the formula -CN.
  • R1", “R2", “R3”, and “Rn” (where n is an integer) used in the present invention may independently have one or more of the groups listed above.
  • R1 is a straight chain alkyl group
  • one hydrogen atom of the alkyl group may be optionally substituted with hydroxyl, alkoxy, alkyl, halogen, etc.
  • the first group may be incorporated within the second group, or the first group may be pendant (ie, attached) to the second group.
  • the amino group may be bonded within the backbone of the alkyl group.
  • the amino group may be attached to the backbone of the alkyl group. The nature of the selected group will determine whether the first group is embedded in or linked to the second group.
  • the compounds described herein may contain "optionally substituted” moieties.
  • substituted (whether preceded by the term “optionally” or not) means that one or more hydrogens of the specified moiety are substituted with a suitable substituent.
  • an "optionally substituted” group may have a suitable substituent at each substitutable position of the group, and when more than one position in any given structure may be selected from one of the specified groups When the above substituents are substituted, the substituents may be the same or different at each position.
  • Combinations of substituents contemplated by this invention are preferably combinations that form stable or chemically feasible compounds. It is also contemplated that, in certain aspects, each substituent may be further optionally substituted (ie, further substituted or unsubstituted) unless expressly stated to the contrary.
  • R1, R2, R3, R4, R5, R, etc. are mentioned several times in the chemical structures and units disclosed and described herein. Any description of R1, R2, R3, R4, R5, R, etc. in the specification applies to any structure or unit referencing R1, R2, R3, R4, R5, R, etc., respectively, unless otherwise stated.
  • the preparation of the present invention contains an organic metal complex represented by formula (I) and one or more solvents.
  • the solvent used is not particularly limited.
  • Unsaturated hydrocarbon solvents well known to those skilled in the art such as toluene, xylene, Mesitylene, tetralin, decalin, dicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.
  • halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, methylene chloride, Dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.
  • halogenated unsaturated hydrocarbon solvents such as chlorobenzene , dichlorobenzene, trichlorobenzene, etc.
  • ether solvents such as tetrahydrofuran, tetrahydropyran, etc. or
  • the invention also provides an organic optoelectronic device, which includes: a first electrode;
  • An organic layer is sandwiched between the first electrode and the second electrode; wherein the organic layer contains the organic metal complex of the present invention.
  • the organometallic complex (platinum, palladium metal compound) of the present invention can effectively reduce the interaction between luminescent molecules due to steric hindrance by introducing a tetradentate ligand unit containing a rigid spiro ring ( Figure 1).
  • the quenching caused by the triplet state improves the luminous efficiency of the device.
  • Applying the organic metal complex of the present invention to organic optoelectronic devices, especially in organic electroluminescent devices can improve the current efficiency of the device, reduce the operating voltage of the device, and extend the life of the device.
  • the organic optoelectronic device can use sputter coating, electron beam evaporation, vacuum evaporation and other methods to evaporate metal or conductive oxides and their alloys on the substrate to form an anode; in the prepared anode
  • the surface is prepared by sequentially evaporating a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport layer, and then evaporating a cathode.
  • organic optoelectronic devices can also be produced by evaporating the cathode, organic layer, and anode in sequence on the substrate.
  • the organic layer can include a hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, etc. Multi-layer structure.
  • the organic layer of the present invention adopts polymer materials according to solvent engineering (spin-coating, tape-casting, doctor-blading, screen-printing, spraying). Ink printing or thermal imaging (Thermal-Imaging, etc.) can replace the evaporation method and can reduce the number of device layers.
  • the materials used in the organic optoelectronic devices according to the present invention can be classified into top-emitting, bottom-emitting or double-sided emitting.
  • the organometallic complex of the present invention can be applied to organic solar cells, lighting OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors and the like on similar principles to organic optoelectronic devices.
  • the OLED device of the present invention contains a hole transport layer.
  • the hole transport material can be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, but does not represent the present invention. Limited to the following structures:
  • the hole transport layer contained in the OLED device of the present invention contains one or more p-type dopants.
  • the preferred p-type dopant of the present invention has the following structure, but it does not mean that the present invention is limited to the following structure:
  • the electron transport layer can be selected from at least one of the following compounds, but this does not mean that the present invention is limited to the following structures:
  • organometallic complex i.e. guest compound represented by formula (I) of the present invention.
  • Ligand 1 was prepared by methods well known in the art.
  • organometallic complex ie, the guest compound
  • luminescent properties of the device are explained in detail in conjunction with the following examples. However, these are only used to illustrate the embodiments of the present invention, and the scope of the present invention is not limited thereto.
  • the evaporated HIL hole injection layer
  • HTL The hole transport layer
  • EBL electrostatic layer
  • EML electrostatic layer
  • the EML electrostatic layer
  • the main material the organic metal complex of the present invention (94: 6, v/v%)
  • the thickness is 35 nm
  • the ETL electrostatic transport layer
  • the cathode Al is evaporated to 70 nm.
  • Examples 1 to 5 show good device performance due to the incorporation of a spiro ring structure into the ligand structure, indicating that the organometallic complex of the present invention has certain application value.

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  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un complexe organométallique, une formulation, un dispositif optoélectronique organique et un appareil d'affichage ou d'éclairage. Le complexe organométallique a une structure représentée par la formule (I) : . Le dispositif photoélectrique organique de la présente invention présente une bonne efficacité d'émission de lumière, une tension d'entraînement réduite et une durée de vie prolongée.
PCT/CN2023/103790 2022-07-29 2023-06-29 Complexe organométallique, formulation, dispositif optoélectronique organique et appareil d'affichage ou d'éclairage WO2024021988A1 (fr)

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CN113717232A (zh) * 2021-09-28 2021-11-30 浙江华显光电科技有限公司 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN114773395A (zh) * 2022-04-27 2022-07-22 浙江华显光电科技有限公司 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN114644660A (zh) * 2022-05-18 2022-06-21 浙江华显光电科技有限公司 有机金属配合物、制剂、有机光电器件及显示或照明装置
CN115286663A (zh) * 2022-07-29 2022-11-04 宇瑞(上海)化学有限公司 有机金属配合物、制剂、有机光电器件及显示或照明装置

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