WO2023024445A1 - 螺环化合物、制剂、有机电致发光二极管及显示装置 - Google Patents
螺环化合物、制剂、有机电致发光二极管及显示装置 Download PDFInfo
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- WO2023024445A1 WO2023024445A1 PCT/CN2022/075574 CN2022075574W WO2023024445A1 WO 2023024445 A1 WO2023024445 A1 WO 2023024445A1 CN 2022075574 W CN2022075574 W CN 2022075574W WO 2023024445 A1 WO2023024445 A1 WO 2023024445A1
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- heteroaryl
- spiro
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- 150000003413 spiro compounds Chemical class 0.000 title claims abstract description 36
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- 239000010410 layer Substances 0.000 claims abstract description 55
- 239000002346 layers by function Substances 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000003003 spiro group Chemical group 0.000 claims description 14
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- 125000005251 aryl acyl group Chemical group 0.000 claims description 10
- 125000005013 aryl ether group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000005104 aryl silyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
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- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005253 heteroarylacyl group Chemical group 0.000 claims description 10
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- 239000001257 hydrogen Substances 0.000 claims description 10
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- 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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- H—ELECTRICITY
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- 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
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- H10K85/658—Organoboranes
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
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- H10K2101/00—Properties of the organic materials covered by group H10K85/00
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- H—ELECTRICITY
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- 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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to a spiro compound, in particular to a spiro compound and an organic electroluminescent diode comprising the compound, belonging to the field of organic photoelectricity.
- organic light-emitting diode As a new type of display technology, organic light-emitting diode (OLED) has self-illumination, wide viewing angle, low energy consumption, high efficiency, thin, rich colors, fast response, wide applicable temperature range, low driving voltage, and flexible
- OLED organic light-emitting diode
- OLED luminescence is divided into two ways: fluorescence luminescence and phosphorescence. According to theoretical speculation, the singlet excited state and triplet excited state formed by charge recombination The ratio is 1:3. Small molecule fluorescent materials can utilize 25% of the energy, and the remaining 75% of the energy is lost due to the non-luminescent mechanism of the triplet excited state, so it is generally believed that the internal quantum efficiency limit of fluorescent materials is 25%.
- MR-TADF multiple resonance-induced thermally activated delayed fluorescence
- MR-TADF molecules Because the skeleton of MR-TADF molecules is a planar structure, molecular stacking is easy to occur under solid-state conditions, and the strong interaction between light-emitting molecules can easily cause aggregation-induced fluorescence quenching, thereby reducing the luminous efficiency of MR-TADF OLED devices.
- the organic electroluminescent diode comprising the organic compound has better efficiency, higher lifetime and reduced driving voltage.
- the object of the present invention is to provide a spiro compound and an organic electroluminescent diode comprising the spiro compound, which has better efficiency and longer life and reduced drive voltage.
- the present invention provides spiro compound, its structure is shown as formula (I):
- a 1 and A 2 are each independently selected from the group consisting of:
- B1, B2, B3, B4, C1, C2 and D1 are each independently selected from a C6-C60 aryl group or a C1-C60 heteroaryl group;
- B1, B2, B3, B4, C1, C2 and D1 can undergo single or multiple substitutions according to the principle of valence bonds
- X is selected from C, O, N, S or Se
- R 1 , R and R 2 are each independently selected from hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl, C1 ⁇ C18 alkoxy, C1 ⁇ C18 alkylsilyl, C1 ⁇ C18 alkoxysilyl, C6 ⁇ C40 substituted or unsubstituted aryl group, C1 ⁇ C40 heteroaryl group, C1 ⁇ C60 substituted or unsubstituted heterospiro ring, C1 ⁇ C60 substituted or unsubstituted spiro ring, substituted or unsubstituted aryl ether group, Substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroaryl group Silyl, substituted or unsubstituted aryloxysilyl, substituted
- the undeuterated groups in the above structures may be partially or fully deuterated.
- said B1, B2, B3 and B4 are each independently selected from the group consisting of:
- R is independently selected from hydrogen, deuterium, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C1-C18 alkoxysilyl, C6-C40 substituted or unsubstituted Aryl, C1 ⁇ C40 heteroaryl, C1 ⁇ C60 substituted or unsubstituted heterospiro ring, C1 ⁇ C60 substituted or unsubstituted spiro ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted Heteroaryl ether, substituted or unsubstituted arylamine, substituted or unsubstituted heteroarylamine, substituted or unsubstituted arylsilyl, substituted or unsubstituted heteroarylsilyl, substituted or Unsubstituted aryloxysilyl, substituted or unsubstituted aryl acyl, substituted or
- the undeuterated groups in the above structures may be partially or fully deuterated.
- said C1 and C2 are each independently selected from the following structures:
- R is selected from hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl, C1 ⁇ C18 alkoxy, C1 ⁇ C18 alkylsilyl, C1 ⁇ C18 alkoxysilyl, C6 ⁇ C40 substituted or unsubstituted aromatic C1-C40 heteroaryl group, C1-C60 substituted or unsubstituted heterospiro ring, C1-C60 substituted or unsubstituted spiro ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted aryl acyl,
- X is selected from C, O, N, S or Se
- Groups that have not been deuterated in the above structure can be partially or fully deuterated;
- the dotted line indicates the formation of a chemical bond with the six-membered ring in the above structure.
- said D1 is selected from the following structures:
- R is selected from hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl, C1 ⁇ C18 alkoxy, C1 ⁇ C18 alkylsilyl, C1 ⁇ C18 alkoxysilyl, C6 ⁇ C40 substituted or unsubstituted aromatic C1-C40 heteroaryl group, C1-C60 substituted or unsubstituted heterospiro ring, C1-C60 substituted or unsubstituted spiro ring, substituted or unsubstituted aryl ether group, substituted or unsubstituted heteroaryl Ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilyl group, substituted or unsubstituted heteroarylsilyl group, substituted or unsubstituted Aryloxysilyl, substituted or unsubstituted aryl acyl,
- X is selected from C, O, N, S or Se
- the undeuterated groups in the above structures may be partially or fully deuterated.
- said A1 and A2 are each independently selected from the group consisting of:
- R can be monosubstituted or multisubstituted according to the principle of valence bond, and R is selected from hydrogen, deuterium, halogen, C1 ⁇ C18 alkyl, C1 ⁇ C18 alkoxy, C1 ⁇ C18 alkylsilyl, C1 ⁇ C18 alkane Oxysilyl, C6 ⁇ C40 substituted or unsubstituted aryl, C1 ⁇ C40 heteroaryl, C1 ⁇ C60 substituted or unsubstituted heterospiro, C1 ⁇ C60 substituted or unsubstituted spiro, substituted or unsubstituted Aryl ether group, substituted or unsubstituted heteroaryl ether group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamine group, substituted or unsubstituted arylsilyl group, substituted or Unsubstituted heteroarylsilyl, substituted or unsubstituted hetero
- X is selected from C, O, N, S or Se
- Dotted line represents to link to form chemical bond with N and B atom among the formula (I);
- the undeuterated groups in the above structures may be partially deuterated or fully deuterated.
- the spiro compound of the present invention is selected from the group consisting of:
- the present invention also provides a preparation, which comprises a spiro compound and at least one solvent.
- the solvent is not particularly limited, and unsaturated hydrocarbon solvents (such as toluene, xylene, mesitylene, tetralin, etc.) well known to those skilled in the art can be used.
- decahydronaphthalene bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, etc.
- saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane , bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, etc.
- unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, etc.
- ether solvents such as tetrahydrofuran, tetrahydropyran, etc.
- ester solvents alkyl benzoate, etc.
- the present invention also provides an organic photoelectric device, which includes: a first electrode;
- the organic functional layer contains the spiro compound.
- the present invention also provides an organic photoelectric device, which comprises a cathode layer, an anode layer and an organic functional layer, the organic functional layer being a hole injection layer, a hole transport layer, a light emitting layer (active layer), a hole blocking layer, an electron injection layer layer and at least one of the electron transport layer, wherein the organic functional layer comprises the spiro compound.
- the organic functional layer is a light-emitting layer, and the light-emitting layer also contains a host compound, wherein,
- the volume ratio of the spiro compound to the host compound is 1:1 to 1:99;
- the host compound is a well-known compound in the art.
- the present invention also provides a display or lighting device comprising the organic electroluminescent diode.
- the organic photoelectric element of the present invention is an organic photovoltaic device, an organic electroluminescent 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 electroluminescent 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 manufacture of the organic photoelectric element of the present invention is as follows: first, metal or conductive oxides and their alloys are deposited on the substrate by methods such as sputter coating, electron beam evaporation, and vacuum evaporation to form an anode; secondly, A hole injection layer, a hole transport layer, a light-emitting layer, a hole blocking layer and an electron transport layer are sequentially evaporated on the surface of the prepared anode, and finally, a cathode is evaporated.
- the organic photoelectric element can also be fabricated by vapor deposition on the substrate in the order of cathode, organic functional layer and anode.
- the organic functional layer is a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer and an electron transport at least one of the layers.
- the organic functional layer in the present invention can also adopt polymer material according to solvent engineering (spin-coating (spin-coating), thin strip forming (tape-casting), doctor-blading (doctor-blading), screen printing (Screen- Printing), inkjet printing or thermal imaging (Thermal-Imaging), etc.) instead of evaporation methods, can reduce the number of device layers.
- the organic photoelectric element of the present invention can be classified as top-emitting, bottom-emitting or double-sided emitting according to the materials used.
- the compounds of the present invention can be applied to electrical devices such as organic solar cells, illuminated OLEDs, flexible OLEDs, organic photoreceptors or organic thin film transistors in a similar principle to organic light-emitting devices.
- the spiro ring structures introduced in the present invention are perpendicular to the MR-TADF plane skeleton (as shown in Figure 2-5 ), so the tight packing between molecules can be suppressed, and the introduction of the spiro ring structure will not greatly change the energy level of the compound (as shown in Table 1), but it reduces the energy level difference of S1-T1, which is beneficial to the three-line State excitons cross the reverse gap, and the oscillator strength (f) also increases, which finally improves the luminous efficiency of MR-TADF materials and improves the thermal stability of luminescent materials.
- This kind of spiro compound is applied to organic optoelectronics Devices, especially in organic electroluminescent devices (organic electroluminescent diodes), can improve current efficiency, reduce the operating voltage of components, and obtain long-life organic electroluminescent diodes.
- the spiro compound of the present invention has good thermal stability, and the introduction of the spiro structure can effectively inhibit the interaction between light-emitting molecules, thereby improving device efficiency.
- the spiro compound of the present invention has better electron and hole accepting ability, and can improve the energy transmission between the host and the guest.
- the spiro compound of the present invention is used as an organic functional layer, especially as an effective light-emitting layer.
- the current efficiency of the electroluminescent device organic electroluminescent diode
- the lighting voltage is reduced, and the life of the device is greatly improved, indicating that most of the electrons and holes are recombined, and the energy is effectively transferred to the spiro compound. Made to glow, not heat.
- FIG. 1 is a schematic structural view of an organic electroluminescent diode of the present invention.
- Figure 2 is a schematic diagram of the HOMO (left) and LUMO (right) hybrid orbitals of compound BN-1;
- Figure 3 is a schematic diagram of the HOMO (left) and LUMO (right) hybrid orbitals of compound BN-2;
- Figure 4 is a schematic diagram of the HOMO (left) and LUMO (right) hybrid orbitals of compound BN-3;
- Figure 5 is a schematic diagram of the HOMO (left) and LUMO (right) hybrid orbitals of compound BN-4.
- the OLED device of the present invention contains a hole transport layer, and the hole transport material can be preferably selected from known materials, particularly preferably selected from the following structures, but it does not mean that the present invention is limited to the following structures:
- the hole transport layer contained in the OLED device of the present invention comprises one or more p-type dopants.
- the preferred p-type dopant of the present invention is the following structure, but it does not mean that the present invention is limited to the following structure:
- the electron transport layer contained in the OLED device of the present invention can be selected from at least one of the following compounds, but it does not mean that the present invention is limited to the following structures:
- the present invention has the general synthetic steps of the compound (guest compound) of structure shown in formula (I) as follows:
- X is Cl, Br or I.
- Embodiment 1 the synthesis of compound 1696
- Embodiment 2 the synthesis of compound 1697
- Embodiment 3 the synthesis of compound 1698
- Embodiment 4 the synthesis of compound 1699
- Embodiment 5 the synthesis of compound 1700
- Embodiment 6 the synthesis of compound 1701
- Embodiment 7 the synthesis of compound 1702
- Embodiment 8 the synthesis of compound 1703
- Embodiment 9 the synthesis of compound 1704
- Embodiment 10 the synthesis of compound 1705
- Embodiment 11 the synthesis of compound 1706
- Embodiment 12 the synthesis of compound 1707
- Embodiment 13 the synthesis of compound 1708
- Embodiment 14 the synthesis of compound 1709
- the organic electroluminescent diode (bottom emission OLED device) of the present invention comprises substrate 110, anode 120, hole injection layer 130, hole transport layer 140, light-emitting layer 150, hole blocking layer 160, electron Transport layer 170 , electron injection layer 180 and cathode 190 .
- Each layer of the organic electroluminescent diode of the present invention can be formed by methods such as vacuum evaporation, sputtering, ion plating, or wet film formation such as spin coating, printing, printing, etc.
- the solvent used is not particularly limited.
- HT-1 and P-3 are co-evaporated or evaporated to form a 10nm hole injection layer (HIL) (wherein, HT-1 and P -3 with a volume ratio of 95:5), a 90nm hole transport layer (HTL), and then evaporate HT-8 on the hole transport layer to form an electron blocking layer (EBL) with a thickness of 10nm, followed by an electron blocking layer (HTL)
- HIL hole injection layer
- HTL 90nm hole transport layer
- EBL electron blocking layer
- HTL electron blocking layer
- EBL electron blocking layer
- EBL electron blocking layer
- EML 35nm light-emitting layer
- ET-13 and LiQ are co-evaporated to form a 35nm electron transport layer (ETL) (wherein, the volume ratio of ET-13 and LiQ is 1:1)
- Examples 1-9 and Comparative Examples 1-2 were characterized by the same standard methods known in the art. Characteristics such as current efficiency, voltage and lifetime according to the above-mentioned examples and comparative examples are shown in Table 2 below.
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Abstract
Description
Claims (10)
- 螺环化合物,所述的螺环化合物的结构如式(I)所示:其中,A 1和A 2各自独立地选自由以下组成的群组:其中,B1、B2、B3、B4、C1、C2和D1各自独立地选自C6~C60的芳基或C1~C60的杂芳基;B1、B2、B3、B4、C1、C2和D1可以进行单取代或多取代;X选自C、O、N、S或Se;虚线表示与式(I)中N和B原子相连形成化学键;R 1、R和R 2各自独立地选自氢、氘、卤素、C1~C18烷基、C1~C18烷氧基、含C1~C18烷硅基、含C1~C18烷氧硅基、C6~C40取代或未取代的芳基,C1~C40的杂芳基、C1~C60取代或未取代的杂螺环、C1~C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基,其中,n为0到10 的整数;上述结构中未被氘代的基团,可以被部分或全部氘代。
- 根据权利要求1所述的螺环化合物,其中,所述的B1、B2、B3和B4各自独立地选自由以下组成的群组:其中,R独立地选自氢、氘、卤素、C1~C18烷基、C1~C18烷氧基、含C1~C18烷硅基、含C1~C18烷氧硅基、C6~C40取代或未取代的芳基,C1~C40的杂芳基、C1~C60取代或未取代的杂螺环、C1~C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基,其中,n为0到10的整数;X选自C、O、N、S或Se;上述结构中未被氘代的基团,可以被部分或全部氘代。
- 根据权利要求1或2所述的螺环化合物,其中,所述的C1和C2各自独立地选自下列结构:其中,R选自氢、氘、卤素、C1~C18烷基、C1~C18烷氧基、含C1~C18烷硅基、含C1~C18烷氧硅基、C6~C40取代或未取代的芳基,C1~C40的杂芳基、C1~C60取代或未取代的杂螺环、C1~C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基,其中,n为0到10的整数;X选自C、O、N、S或Se;虚线表示与权利要求2中所述的六元环相连形成化学键;上述结构中未被氘代的基团,可以被部分或全部氘代。
- 根据权利要求1或2所述的螺环化合物,其中,所述的D1选自下列结构:其中,R选自氢、氘、卤素、C1~C18烷基、C1~C18烷氧基、含C1~C18烷硅基、含C1~C18烷氧硅基、C6~C40取代或未取代的芳基,C1~C40的杂芳基、C1~C60取代或未取代的杂螺环、C1~C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基,其中,n为0到10的整数;X选自C、O、N、S或Se;上述结构中未被氘代的基团,可以被部分或全部氘代。
- 根据权利要求1或2所述的螺环化合物,其中,所述的A 1和A 2各自独立地选自由以下组成的群组:其中,R选自氢、氘、卤素、C1~C18烷基、C1~C18烷氧基、含C1~C18烷硅基、含C1~C18烷氧硅基、C6~C40取代或未取代的芳基,C1~C40的杂芳基、C1~C60取代或未取代的杂螺环、C1~C60取代或未取代的螺环、取代或未取代的芳基醚基、取代或未取代的杂芳基醚基、取代或未取代的芳基胺基、取代或未取代的杂芳基胺基、取代或未取代的芳基硅基、取代或未取代的杂芳基硅基、取代或未取代的芳基氧硅基、取代或未取代的芳基酰基、取代或未取代的杂芳基酰基或取代或未取代的氧膦基,其中,n为0到10的整数;X选自C、O、N、S或Se;虚线表示与式(I)中N和B原子相连形成化学键;上述结构中未被氘代的基团可被部分氘代或全氘代。
- 制剂,其包含权利要求1或2所述的螺环化合物和至少一种溶剂,其中,所述溶剂为饱和烃溶剂、不饱和烃溶剂、醚类溶剂或酯类溶剂。
- 有机电致发光二极管,其包括阴极层、阳极层和有机功能层,所述有机功能层为空穴注入层、空穴传输层、发光层、空穴阻挡层、电子注入层和电子传输层,其中,所述有机功能层包含权利要求1或2所述的螺环化合物。
- 根据权利要求8所述的有机电致发光二极管,其中,所述有机功能层为发光层,所述发光层中还包含主体化合物,其中,所述螺环化合物与所述主体化合物的体积比为1:1~1:99。
- 显示装置,其包括权利要求8所述的有机电致发光二极管。
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- 2022-02-09 JP JP2023547277A patent/JP2024507467A/ja active Pending
- 2022-02-09 EP EP22859804.1A patent/EP4276103A1/en active Pending
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CN113416206A (zh) * | 2021-08-23 | 2021-09-21 | 浙江华显光电科技有限公司 | 螺环化合物、制剂、有机电致发光二极管及显示装置 |
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CN116903651A (zh) * | 2023-09-07 | 2023-10-20 | 浙江华显光电科技有限公司 | 一种含硒发光化合物及在电子器件中的应用 |
CN116903651B (zh) * | 2023-09-07 | 2023-12-15 | 浙江华显光电科技有限公司 | 一种含硒发光化合物及在电子器件中的应用 |
CN116874517A (zh) * | 2023-09-08 | 2023-10-13 | 浙江华显光电科技有限公司 | 含硒吩化合物及其在有机发光装置的应用 |
CN116874517B (zh) * | 2023-09-08 | 2023-12-01 | 浙江华显光电科技有限公司 | 含硒吩化合物及其在有机发光装置的应用 |
CN117946146A (zh) * | 2024-03-27 | 2024-04-30 | 浙江华显光电科技有限公司 | 含咪唑及衍生基团的硼氮化合物、有机电致发光器件及应用 |
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CN113416206A (zh) | 2021-09-21 |
JP2024507467A (ja) | 2024-02-20 |
KR20230145473A (ko) | 2023-10-17 |
CN113416206B (zh) | 2022-03-15 |
EP4276103A1 (en) | 2023-11-15 |
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