WO2023221997A1 - Composé et son utilisation - Google Patents

Composé et son utilisation Download PDF

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Publication number
WO2023221997A1
WO2023221997A1 PCT/CN2023/094605 CN2023094605W WO2023221997A1 WO 2023221997 A1 WO2023221997 A1 WO 2023221997A1 CN 2023094605 W CN2023094605 W CN 2023094605W WO 2023221997 A1 WO2023221997 A1 WO 2023221997A1
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substituted
unsubstituted
group
ring
compound
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PCT/CN2023/094605
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Chinese (zh)
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徐增
游劲松
李祯龙
张翰
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华为技术有限公司
四川大学
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Publication of WO2023221997A1 publication Critical patent/WO2023221997A1/fr

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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
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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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • Y02E10/549—Organic PV cells

Definitions

  • the present application relates to the technical field of organic light-emitting materials, and in particular to a compound and its application.
  • Organic light-emitting materials have good luminescence properties, good adjustability, relatively flexible molecular design, and can be coated on various substrates to form films. Therefore, they are widely used in organic electroluminescent devices (Organic Light Emission Diodes, OLEDs). , organic light-emitting field effect transistors, organic photovoltaic devices, luminescent electrochemical cells, photoelectric converters, light-operated devices, image sensors, lasers, photosensitive devices, biological imaging equipment, coatings, organic laser equipment and other fields. Among them, an organic electroluminescent device is an energy conversion device that uses organic luminescent materials as luminescent materials and can convert applied electrical energy into light energy.
  • OLEDs Organic Light Emission Diodes
  • embodiments of the present application provide a compound that has good luminescent properties and can improve the performance of light-emitting devices.
  • the first aspect of the embodiments of the present application provides a compound, which is a polymer with a structure shown in formula (1):
  • M 2 and M 3 are respectively substituted or unsubstituted aromatic ring, substituted or unsubstituted heteroaromatic ring, or substituted or unsubstituted aliphatic ring;
  • Z is C(R 1 ),
  • Y is NR 2 , O, S or Se;
  • each occurrence of R 1 and R 2 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted Heterocycloalkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cyclo
  • the compound provided in the embodiments of the present application is a polymer with a structure represented by formula (1).
  • the molecular structure of the compound contains two or more structures represented by formula (1), so that the compound has good luminescence properties and is easy to synthesis.
  • the compound has a fused ring structure composed of a boron atom, a Y group, a naphthalene ring, etc. as the skeleton center.
  • the fused ring structure skeleton center can produce a good resonance effect, with a large resonance area and strong resonance effect, and the fused ring
  • the structure has high electrical stability; at the same time, the skeleton center of the fused ring structure is a rigid skeleton structure, which can effectively reduce the relaxation degree of its excited state structure, so that the compound can obtain a higher fluorescence quantum yield and a narrower half-peak width ( FWHM, Full Width at Half Maxima), and appropriate HOMO (Highest Occupied Molecular Orbital, highest occupied molecular orbital) and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy levels.
  • FWHM Full Width at Half Maxima
  • the compounds described in the embodiments of the present application have high structural stability, high electrical stability, high fluorescence quantum yield, and narrow half-peak width. When used as luminescent materials in light-emitting devices, they can improve device efficiency, luminescent color purity, and device stability.
  • the luminescence peak position of the compound can be further adjusted, and more different luminescence colors (such as red light, green light, blue light) and different luminescence colors can be obtained.
  • Compounds with different behaviors expand the scope of applications.
  • the compound is a polymer of 2-6 structures represented by the formula (1). More different compounds can be obtained by using different amounts of the structure represented by formula (1).
  • the compound has any general structural formula represented by formula (I) to formula (X):
  • Z is C (R 1 ), Y is NR 2 , O, S or Se; R 1 and R 2 are independently selected from hydrogen atoms, deuterium atoms and tritium atoms each time they appear.
  • halogen atom substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkenyl group, substituted or Unsubstituted heterocycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl Oxy group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted alkylamine group, substituted or unsubstituted ary
  • the substituents in the arylamine group, substituted heteroarylamino group, substituted borane group, substituted silyl group, and substituted aromatic silicon group include deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, Sulfonic acid group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloal
  • the substituted or unsubstituted alkyl group is a substituted or unsubstituted C 1 -C 30 alkyl group;
  • the substituted or unsubstituted cycloalkyl group is a substituted or unsubstituted C 3 -C 30 cycloalkyl group.
  • the substituted or unsubstituted heterocycloalkyl group is a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group;
  • the substituted or unsubstituted alkenyl group is a substituted or unsubstituted C 2 -C 30 alkenyl group;
  • the substituted or unsubstituted cycloalkenyl is a substituted or unsubstituted C 3 -C 10 cycloalkenyl;
  • the substituted or unsubstituted heterocycloalkenyl is a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl;
  • the substituted or unsubstituted alkynyl group is a substituted or unsubstituted C 2 -C 30 alkynyl group;
  • the substituted or unsubstituted cycloalkynyl group is a substituted or unsubstituted C 6 -
  • the C 1 -C 18 electron-withdrawing group containing at least one heteroatom among O, N, S, B, P, and F includes substituted or unsubstituted acyl groups. Imine group, substituted or unsubstituted amide group, cyano group, nitro group or hydroxyl.
  • each occurrence of R 1 and R 2 is independently a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, or a tritiated methyl group.
  • fluoropropyl trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, Tritiated tert-butyl, phenyl-substituted tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritium Phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether group, methyl substituted diphenyl Ether group, naphth
  • the ring structure formed includes any of the formulas (a) to (i):
  • the positions marked with * are connection positions, and the structures of formulas (a) to (i) are connected in a parallel ring manner through the positions marked with *. Connecting adjacent R 1 to form the above-mentioned ring structure can not only enrich the types of compounds and enable better applications, but also enable the compounds to obtain good luminescence properties and facilitate preparation.
  • the ring structure formed includes the structures represented by formulas (A) to (D):
  • R 5 is a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, n is an integer from 0 to 4;
  • the formula (A) to In formula (D) are connection positions, and the structures of formulas (A) to (D) are connected in a parallel ring manner through the positions marked with *.
  • R 2 is connected to the adjacent R 1 to form the above-mentioned ring
  • the structure can not only enrich the types of compounds and better realize their applications, but also enable the compounds to obtain good luminescent properties and be easy to prepare.
  • the compound includes any one of the compounds with structural formulas such as formulas (1)-(268):
  • the second aspect of the embodiments of this application provides the use of the compounds and their salts described in the first aspect in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, luminescent electrochemical cells, photoelectric converters, light switching devices, image sensors, and lasers. , photosensitive devices, biological imaging equipment, coatings, and applications in organic laser equipment.
  • the compounds in the embodiments of the present application have good luminescent properties and can improve the performance of light-emitting devices.
  • a third aspect of the embodiments of the present application provides a luminescent layer, which includes the compound described in the first aspect.
  • the compounds in the embodiments of the present application have good luminescent properties and can improve the performance of light-emitting devices.
  • the light-emitting layer includes a host material and a doping material
  • the doping material includes the compound.
  • the compounds in the embodiments of the present application have a smaller Stoke shift and can be used as doping materials to better sensitize host materials that emit visible light.
  • the fourth aspect of the embodiments of the present application provides an electronic device, which includes the compound described in the first aspect; or includes the light-emitting layer described in the third aspect.
  • the compounds in the embodiments of the present application have good luminescent properties and can improve the performance of light-emitting devices.
  • the electronic device includes a cathode and an anode, and a functional layer located between the cathode and the anode, and the functional layer includes the compound.
  • the electronic device includes an electroluminescent device, an organic light-emitting field effect transistor, an organic photovoltaic device or a luminescent electrochemical cell.
  • a fifth aspect of the embodiment of the present application provides a display device, which includes the electronic device described in the fourth aspect; or includes the light-emitting layer described in the third aspect.
  • the compounds in the embodiments of the present application have good luminescence properties and are beneficial to improving the display effect of the display device.
  • An embodiment of the present application further provides an electronic device, characterized in that the electronic device includes the display device described in the fifth aspect; or includes the electronic device described in the fourth aspect.
  • the compounds in the embodiments of the present application have good luminescent properties, which are beneficial to improving the display effect of electronic equipment and improving the market competitiveness of electronic equipment.
  • An embodiment of the present application also provides a lighting device, characterized in that the lighting device includes the electronic device described in the fourth aspect; or includes the luminescent layer described in the third aspect.
  • the compounds in the examples of this application have good luminescent properties and have It is beneficial to improve the luminous effect of the lighting device and improve the market competitiveness of the lighting device.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device 100 provided by an embodiment of the present application.
  • Figure 2 is a schematic structural diagram of a display device 200 provided by an embodiment of the present application.
  • Figure 3 is a schematic structural diagram of an electronic device 300 provided by an embodiment of the present application.
  • Figure 4 is a high-resolution mass spectrum of compound 4 prepared in Example 1 of the present application.
  • Figures 5 and 6 are respectively the hydrogen nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum of compound 4 prepared in Example 1 of the present application;
  • Figure 7 is the ultraviolet absorption spectrum and fluorescence spectrum of compound 4 in Example 1 of the present application.
  • Figure 8 is a hydrogen nuclear magnetic resonance spectrum of compound 32 prepared in Example 2 of the present application.
  • Figure 9 is the fluorescence spectrum of compound 32 in Example 2 of the present application.
  • Figure 10 is the hydrogen nuclear magnetic resonance spectrum of compound 139 prepared in Example 3 of the present application.
  • Figure 11 is the ultraviolet absorption spectrum and fluorescence spectrum of compound 139 in Example 3 of the present application.
  • Figure 12 is a schematic structural diagram of the organic electroluminescent device 100 of Device Embodiment 1;
  • Figure 13 is a luminescence spectrum diagram of the device of Device Embodiment 1 and Device Embodiment 2 of the present application;
  • Figure 14 is a current density-voltage-brightness diagram of the devices of Device Embodiment 1 and Device Embodiment 2 of the present application;
  • Figure 15 is a brightness-external quantum efficiency diagram of the devices of Device Example 1 and Device Example 2 of the present application.
  • FIG. 1 is a schematic structural diagram of an organic electroluminescent device (OLEDs) 100 provided by an embodiment of the present application.
  • the organic electroluminescent device 100 shown in FIG. 1 includes an anode 10, a cathode 20, and a functional layer 30 located between the anode 10 and the cathode 20.
  • the functional layer 30 includes a light-emitting layer 301. After a certain voltage is applied between the anode 10 and the cathode 20 of the organic electroluminescent device 100, the luminescent material in the luminescent layer 301 is excited to emit light through the recombination of holes and electrons in the luminescent layer 301, thus imparting a certain effect.
  • the electromechanical luminescent device 100 emits light.
  • the luminescent material in the luminescent layer 301 needs to have high luminous efficiency, stable properties, and high luminous color purity to meet the requirements. Higher demanding display standards.
  • embodiments of the present application provide a compound that can be used in the above-mentioned light-emitting layer 301 to enable the organic electroluminescent device to obtain good light-emitting performance, and the compound is easy to prepare.
  • the above-mentioned compound will be introduced in detail below.
  • the compound is a boron-containing organic compound.
  • the compound is a polymer with the structure shown in formula (1):
  • M 2 and M 3 are respectively substituted or unsubstituted aromatic ring, substituted or unsubstituted heteroaromatic ring, or substituted or unsubstituted aliphatic ring;
  • Z is C(R 1 ),
  • Y is NR 2 , O, S or Se;
  • each occurrence of R 1 and R 2 is independently selected from a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted Heterocycloalkanes group, substituted or unsubstituted alkenyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted
  • the compounds provided in the embodiments of the present application are polymers of the structure represented by formula (1).
  • the molecular structure of the compound contains two or more structures represented by formula (1). Since the structure represented by formula (1) has the following properties: The No. 1 ring of the B atom and the Y atom (or group), the No. 1 ring is a boron heterocyclic ring, and the naphthalene ring is introduced into the No. 2 ring through ring synthesis, and at the same time, under the joint action of the M 2 ring and the M 3 ring , so that the compound has good luminescence properties and is easy to synthesize.
  • M 2 and M 3 are respectively a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring; specifically, substituted or The unsubstituted aromatic ring may be a substituted or unsubstituted C 6 -C 30 aromatic ring, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, a substituted or unsubstituted phenanthrene ring, substituted or unsubstituted diphenyl ring, substituted or unsubstituted terphenyl ring, substituted or unsubstituted binaphthyl ring, substituted or unsubstituted fluorene ring,
  • the substituents in the substituted aromatic ring, substituted heteroaromatic ring, and substituted aliphatic ring include deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, Sulfonic acid group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted Or one or more of unsubstituted heteroaryl, substituted or unsubstituted amino.
  • M 2 and M 3 are respectively a benzene ring, a deuterated benzene ring, a tritiated benzene ring, a methyl-substituted benzene ring, an ethyl-substituted benzene ring, an isopropyl-substituted benzene ring, a tert.
  • the compound is a multimer of 2-6 structures represented by formula (1).
  • the compound can be 2, 3, 4, 5 or 6 polymers represented by formula (1).
  • the structure of the polymer is not limited to 2, 3, 4, 5 or 6 polymers represented by formula (1).
  • the compounds provided in the embodiments of the present application may have a variety of structural forms. Multiple structures represented by formula (1) in the compound may be connected in different ways, specifically by sharing certain ring structures or through certain ring structures. Connected to each other through a ring or through a connecting group, etc. For example, in some embodiments, multiple structures represented by formula (1) in the compound can be connected through a shared naphthalene ring, a shared M 2 ring, a shared M 3 ring, etc.; in some embodiments, multiple structures represented by formula (1) in the compound ) can be connected through No. 1 ring and ring, M 2 ring and ring, No.
  • multiple structures represented by formula (1) in the compound can be connected through a single Bond, phenylene, aromatic ring, aromatic heterocyclic ring, alicyclic ring, or aliphatic heterocyclic connecting group to achieve connection.
  • the compound may have any general structural formula represented by formula (I) to formula (X):
  • Z is C (R 1 ), Y is NR 2 , O, S or Se; R 1 and R 2 are independently selected from hydrogen atoms, deuterium atoms and tritium atoms each time they appear.
  • halogen atom substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted heterocycloalkyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted cycloalkenyl group, substituted or Unsubstituted heterocycloalkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl Oxy group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted heteroaryloxy group, substituted or unsubstituted alkylamine group, substituted or unsubstituted ary
  • the compound provided in the embodiment of the present application has a fused ring structure composed of boron atoms, Y groups, naphthalene rings, etc. as the skeleton center.
  • the fused ring structure skeleton center can produce a good resonance effect, with a large resonance area and a strong resonance effect.
  • the fused ring structure has high electrical stability; at the same time, the skeleton center of the fused ring structure is a rigid skeleton structure, which can effectively reduce the relaxation degree of its excited state structure, thereby enabling the compound to obtain a higher fluorescence quantum yield and a narrower Full Width at Half Maxima (FWHM, Full Width at Half Maxima), and appropriate HOMO (Highest Occupied Molecular Orbital, highest occupied molecular orbital) and LUMO (Lowest Unoccupied Molecular Orbital, lowest unoccupied molecular orbital) energy levels; in addition, this application
  • the compounds of the examples have a small Stoke shift and can play a good sensitizing effect on materials that emit visible light.
  • half peak width refers to the peak width at half the height of the luminescence peak in the electroluminescence spectrum of the luminescent material.
  • the compounds of the embodiments of the present application can achieve a half-peak width of less than 30 nm.
  • the compounds described in the embodiments of this application have high structural stability, high electrical stability, high fluorescence quantum yield, and narrow half-peak width as luminescent materials in light-emitting devices, the device efficiency, luminescent color purity, and device stability can be improved.
  • the luminescence peak position of the compound can be further adjusted, and more different luminescence colors (such as red light, green light, blue light) and different luminescence colors can be obtained.
  • Compounds with different behaviors expand the scope of applications.
  • the light-emitting position of the compound can be adjusted to the green light area.
  • green is used as the main light-emitting color, providing about 60% of the brightness of the full screen.
  • the above-mentioned compound emits green light, it is more conducive to its use in OLED- Full-color light-emitting devices of RGB three primary colors and OLED white light lighting are widely used in fields.
  • the compounds in the embodiments of the present application can be obtained through a relatively simple synthesis route and can be synthesized without using dangerous chemicals such as butyllithium. They are suitable for industrial production and have good application effects and industrialization in the field of OLED lighting or OLED display. prospect.
  • Z is represented by C(R 1 ); wherein, R 1 can be a group with the same structure or a group with a different structure each time it appears. That is, Z at different positions may have the same structure or different structures. Specifically, Z at all positions may be the same, or Z at all positions may be different, or Z at some positions may be the same. For example, in some embodiments, in Formula (I) to Formula (X), all Z are C(H), or some Z are C(H) and the remaining Z are -C(CH 3 ).
  • Y in Formula (I) to Formula (X), Y can be a group with the same structure or different each time it appears.
  • the structural groups that is, multiple Ys, may be groups of the same structure or groups of different structures.
  • multiple Ys when multiple Ys are groups with the same structure, multiple Ys can be O, S, N (R 2 ), or Se; in this case, boron-containing organic compounds are easier to synthesize, and the symmetry of the compounds is more
  • the high, symmetrical rigid skeleton structure is more conducive to reducing the relaxation degree of the excited state structure of the compound and obtaining a narrower half-peak width.
  • they can be completely different types of groups.
  • the compound contains two Y, for example, one Y can be S or O or Se, and the other Y can be N ( R 2 ), or one Y is O and the other Y is S; it can also be the same type of group with different structures, for example, both Y are N (R 2 ), but R 2 is different.
  • the two Y's in formula (I) to formula (X) all contain heteroatoms, which are more conducive to producing a strong resonance effect with the two boron atoms in the structural formula.
  • the substituents in the amino group, substituted arylamine group, substituted heteroarylamino group, substituted borane group, substituted silyl group, and substituted aromatic silicon group include deuterium atoms, tritium atoms, halogen atoms, and cyano groups, Nitro, carboxyl, sulfonate, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted
  • the heteroatoms in the heterocycloalkyl group, heterocycloalkenyl group, heterocycloalkynyl group, heteroaryl group, heteroaryloxy group and heteroarylamino group can be selected from oxygen atoms, sulfur atoms, and nitrogen atoms. , one or more of selenium atoms.
  • the above-mentioned substituted or unsubstituted alkyl group is a chain alkyl group, which can be a linear alkyl group or a branched alkyl group.
  • the substituted or unsubstituted alkyl group can be a substituted or unsubstituted alkyl group.
  • the substituted or unsubstituted alkyl group can be a substituted or unsubstituted C 1 -C 10 chain alkyl group, a substituted or unsubstituted C 1 -C 6 chain alkyl group, for example, it can be a substituted or unsubstituted C 1 -C 6 chain alkyl group.
  • the substituents in the substituted alkyl group may be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic acid groups, acyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted Cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl.
  • the substituted alkyl group can be deuterated methyl, tritiated methyl, fluoroethyl, fluoropropyl, trifluoromethyl, deuterated ethyl, tritiated ethyl, deuterated isopropyl , tritiated isopropyl, deuterated tert-butyl, tritiated tert-butyl, phenyl-substituted tert-butyl, etc.
  • the above-mentioned substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C 3 -C 30 cycloalkyl group.
  • the substituted or unsubstituted cycloalkyl group can be a substituted or unsubstituted C 4 to C 12 cycloalkyl group, a substituted or unsubstituted C 5 to C 6 cycloalkyl group, for example, it can be a substituted or unsubstituted cycloalkyl group.
  • the substituents in the substituted cycloalkyl can be but are not limited to deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitrogen atoms, etc. group, carboxyl group, sulfonic acid group, acyl group, alkyl group, alkoxy group.
  • the substituted cycloalkyl group may be deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, and the like.
  • the above-mentioned substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group.
  • the substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted C 4 -C 12 heterocycloalkyl group, or a substituted or unsubstituted C 5 -C 6 heterocycloalkyl group.
  • the substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted aziridine, a substituted or unsubstituted azetidine, or a substituted or unsubstituted azetidine.
  • the above-mentioned substituted or unsubstituted alkenyl group may be a substituted or unsubstituted C 2 -C 30 alkenyl group; it may be a straight chain alkenyl group or a branched chain alkenyl group.
  • the substituted or unsubstituted alkenyl group can be a substituted or unsubstituted C 2 -C 10 chain alkenyl group, a substituted or unsubstituted C 2 -C 6 chain alkenyl group, for example, it can be a substituted or unsubstituted C 2 -C 6 chain alkenyl group.
  • the substituent in the substituted alkenyl group may be, but is not limited to, a deuterium atom or a tritium atom. ion, halogen atom, cyano group, nitro group, carboxyl group, sulfonic acid group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted Aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl.
  • the substituted alkenyl group may be deuterated vinyl, tritiated vinyl, fluorovinyl, fluoropropenyl, etc.
  • the above-mentioned substituted or unsubstituted cycloalkenyl group may be a substituted or unsubstituted C 3 -C 10 cycloalkenyl group.
  • the substituted or unsubstituted cycloalkenyl group may be a substituted or unsubstituted C 4 -C 7 cycloalkenyl group, a substituted or unsubstituted C 5 -C 6 cycloalkenyl group, for example, it may be a substituted or unsubstituted cycloalkenyl group.
  • the substituents in the substituted cycloalkenyl group may be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic acid groups, acyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl.
  • the substituted cycloalkenyl group may be fluorinated cyclopentenyl, fluorinated cyclohexenyl, etc.
  • the above-mentioned substituted or unsubstituted heterocyclic alkenyl group may be a substituted or unsubstituted C 2 -C 10 cycloalkenyl group.
  • the substituted or unsubstituted heterocyclic alkenyl group may be a substituted or unsubstituted C 3 -C 6 heterocyclic alkenyl group, a substituted or unsubstituted C 4 -C 5 heterocyclic alkenyl group, for example, it may be Substituted or unsubstituted azocyclopentadiene, substituted or unsubstituted oxane, etc.
  • the substituents in the substituted heterocyclic alkenyl group may be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonate groups, acyl groups, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkyl groups.
  • the substituted heterocycloalkenyl group may be fluorocyclopentadienyl, fluorooxacyclohexenyl, etc.
  • the substituted or unsubstituted alkynyl group may be a substituted or unsubstituted C 2 -C 30 alkynyl group; it may be a straight chain alkynyl group or a branched chain alkynyl group.
  • the substituted or unsubstituted alkynyl group can be a substituted or unsubstituted C 2 -C 10 chain alkynyl group, a substituted or unsubstituted C 2 -C 6 chain alkynyl group, for example, it can be a substituted or Unsubstituted ethynyl, substituted or unsubstituted propynyl, etc.
  • the substituent in the substituted alkynyl group may be, but is not limited to, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, a carboxyl group, a sulfonic acid group, an acyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted Cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl.
  • the substituted alkynyl group may be deuterated ethynyl, tritiated ethynyl, fluoroethynyl, fluoropropynyl, etc.
  • the substituted or unsubstituted cycloalkynyl group may be a substituted or unsubstituted C 6 -C 10 cycloalkynyl group.
  • the substituted or unsubstituted heterocycloalkynyl group may be a substituted or unsubstituted C 5 -C 10 heterocycloalkynyl group.
  • the above-mentioned substituted or unsubstituted alkoxy group can be a substituted or unsubstituted C 1 -C 30 alkoxy group, and can be a linear alkoxy group or a branched alkoxy group; some In embodiments, the substituted or unsubstituted alkoxy group may be a substituted or unsubstituted C 1 -20 alkoxy group, C 1 -C 10 alkoxy group, or C 1 -C 6 alkoxy group.
  • the substituted or unsubstituted alkoxy group may be substituted or unsubstituted methoxy (-OCH 3 ), substituted or unsubstituted ethoxy (-OCH 2 CH 3 ), substituted or unsubstituted tert-butyl Oxygen etc.
  • the substituents in the substituted alkoxy group may be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonate groups, acyl groups, alkyl groups, alkoxy groups, cycloalkyl groups, and the like.
  • the above-mentioned substituted or unsubstituted aryl group may be a substituted or unsubstituted C 6 -C 30 aryl group; the substituted or unsubstituted aryl group may be a substituted or unsubstituted C 6 -C 30 aryl group.
  • the aryl group can be a monocyclic aryl group or a polycyclic aryl group.
  • the substituted or unsubstituted aryl group may be a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 12 aryl group.
  • the substituents in the substituted aryl group can be deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic acid groups, acyl groups, and substituted or unsubstituted alkyl groups, cycloalkyl groups, and alkoxy groups. , aryl, aryloxy, heteroaryl, etc.
  • Substituted or unsubstituted monocyclic aryl groups may be, for example, phenyl, deuterated phenyl, tritiated phenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl Substituted phenyl, deuterated methyl substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, etc.
  • the polycyclic aromatic group can be a fused ring type or Non-fused ring type (such as biphenyls).
  • the substituted or unsubstituted polycyclic aromatic group of biphenyls can be, but is not limited to, a substituted or unsubstituted diphenyl group, terphenyl group, or diphenyl ether group (two benzene rings connected through an oxygen atom) .
  • the substituted polycyclic aromatic group may be deuterated diphenyl, tritiated diphenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, Deuterated tert-butyl-substituted diphenyl, deuterated terphenyl, tritiated terphenyl, methyl-substituted diphenyl ether group, etc.
  • the substituted or unsubstituted polycyclic aryl group of the fused ring type can be a substituted or unsubstituted naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, fluorenyl group, spirofluorenyl group, 9,9-dimethylfluorenyl group, bifluorenyl group, etc. Naphthyl, binaphthylfluorenyl, etc.
  • the above-mentioned substituted or unsubstituted aryloxy group may be a substituted or unsubstituted C 6 -C 30 aryloxy group; the aryloxy group may be a monocyclic aryloxy group or a polycyclic aryloxy group.
  • the substituted or unsubstituted aryloxy group may be a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 6 -C 12 aryloxy group.
  • it may be an aryloxy group obtained by the above-mentioned oxidation of an aryl group.
  • the above-mentioned substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C 3 -C 30 heteroaryl group.
  • the substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C 5 -C 20 heteroaryl group, a substituted or unsubstituted C 6 -C 12 heteroaryl group.
  • the heteroatoms in the heteroaryl group can be selected from one or more types of N, O, S, and Se atoms.
  • the substituted or unsubstituted heteroaryl may be a substituted or unsubstituted five-membered heterocycle, a substituted or unsubstituted six-membered heterocycle, a substituted or unsubstituted benzoheterocycle, a substituted or unsubstituted heterocycle and heterocycle wait.
  • the substituted or unsubstituted heteroaryl may be pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, benzofuryl, dibenzofuryl, tert-butyl-substituted dibenzoyl.
  • the above-mentioned substituted or unsubstituted heteroaryloxy group may be a substituted or unsubstituted C 3 -C 30 heteroaryloxy group.
  • the substituted or unsubstituted heteroaryloxy group may be a substituted or unsubstituted C 5 -C 20 heteroaryloxy group, a substituted or unsubstituted C 6 -C 12 heteroaryloxy group.
  • the heteroatoms in the heteroaryloxy group can be selected from one or more types of N, O, S, and Se atoms. Specifically, the heteroaryloxy group can be obtained by oxidation of the above-mentioned heteroaryl group, which will not be described again here.
  • the substituted or unsubstituted alkylamino group is an amino group substituted by a substituted or unsubstituted alkyl group.
  • the substituted or unsubstituted alkylamino group may be a substituted or unsubstituted C 1 -C 30 alkylamino group.
  • the substituted or unsubstituted alkylamino group may be a substituted or unsubstituted C 2 -C 20 alkylamino group, a substituted or unsubstituted C 3 -C 12 alkylamino group.
  • the substituted or unsubstituted alkylamino group may be ethylamino and the like.
  • the substituted or unsubstituted arylamine group is an amino group substituted by a substituted or unsubstituted aryl group. Specifically, it may be an amino group substituted by the above-mentioned substituted or unsubstituted aryl group.
  • the substituted or unsubstituted arylamine group may be a substituted or unsubstituted C 6 -C 30 arylamine group.
  • the substituted or unsubstituted arylamine group may be a substituted or unsubstituted C 6 -C 20 arylamine group, a substituted or unsubstituted C 7 -C 15 arylamine group.
  • the substituted or unsubstituted arylamine group may be, for example, phenylamino, dimethylphenylamino, tert-butylbenzene-substituted amino, di-tert-butylphenylamino, etc.
  • the above-mentioned substituted or unsubstituted heteroarylamino group is an amino group substituted by a substituted or unsubstituted heteroaryl group. Specifically, it may be an amino group substituted by the above-mentioned substituted or unsubstituted heteroaryl group.
  • the substituted or unsubstituted heteroarylamino group may be a substituted or unsubstituted C 3 -C 30 heteroarylamino group.
  • the substituted or unsubstituted heteroarylamino group may be a substituted or unsubstituted C 5 -C 20 heteroarylamino group, or a substituted or unsubstituted C 6 -C 12 heteroarylamino group.
  • the above-mentioned substituted or unsubstituted borane group may be a borane group, a phenyl-substituted borane group, etc., and the substituent in the substituted borane group may be a deuterium atom, a tritium atom, a halogen atom, or a cyanide atom.
  • the substituted or unsubstituted silyl group may be trimethylsilyl group or the like.
  • the substituted or unsubstituted aromatic silicon group may be phenyl silicon group or the like.
  • C 1 -C 18 electron-withdrawing groups containing at least one heteroatom among O, N, S, B, P, and F may include, but are not limited to, substituted or unsubstituted.
  • the substituents in the substituted imide group and the substituted amide group can be, but are not limited to, deuterium atoms, tritium atoms, halogen atoms, cyano groups, nitro groups, carboxyl groups, sulfonic acid groups, acyl groups, substituted or unsubstituted Alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl.
  • each occurrence of R 1 and R 2 can independently be a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, Fluoropropyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritium Substituted tert-butyl, phenyl-substituted tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohex
  • some adjacent R 1s are connected to form a ring, and the remaining R 1s can be independently selected from the above optional groups.
  • the ring structure formed includes but is not limited to any one shown in formula (a) to formula (i):
  • the positions marked with * are connection positions, and the structures of formulas (a) to (i) are connected in a parallel ring manner through the positions marked with *.
  • the compounds represented by formula (a) to (i) please refer to the compound represented by formula (7) below; for the case corresponding to formula (b), please refer to the compound represented by formula (9) below; for the case corresponding to formula (c), please refer to the following formula
  • the substitutable position may have a substituent, and the substituent may be, for example, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a nitro group, Carboxyl group, sulfonate group, acyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group , substituted or unsubstituted heteroaryl, etc.
  • the different structures shown in the above formulas (a) to (i) are beneficial to the controllable adjustment of the light color of the compound.
  • R 1 and R 2 are connected to form a ring.
  • One or more R 1 may participate in the ring formation, and the remaining R 1 not participating in the ring formation may be independently selected from the above optional groups.
  • the ring structure formed may include structures shown in formulas (A) to (D):
  • R 5 is a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, n is an integer from 0 to 4;
  • the formula (A) to In formula (D) are connection positions, and the structures of formulas (A) to (D) are connected in a parallel ring manner through the positions marked with *.
  • the compound corresponding to the situation of formula (A) can be a compound represented by formula (II-A), and also see the compound represented by formula (115) below;
  • the compounds represented by formula (I) to formula (X) may specifically include any one of the compounds represented by structural formulas such as formulas (1)-(268):
  • the compound represented by general formula (I) can be synthesized according to the following steps:
  • the compound represented by general formula (II) can be synthesized according to the following steps:
  • the compound represented by general formula (III) can be synthesized according to the following steps:
  • the compound represented by general formula (IV) can be synthesized according to the following steps:
  • the compound represented by general formula (V) can be synthesized according to the following steps:
  • the compound represented by general formula (VI) can be synthesized according to the following steps:
  • the compound represented by general formula (VII) can be synthesized according to the following steps:
  • the compound represented by general formula (VIII) can be synthesized according to the following steps:
  • the compound represented by general formula (IX) can be synthesized according to the following steps:
  • the compound represented by general formula (X) can be synthesized according to the following steps:
  • the above-mentioned compounds provided in the embodiments of the present application have high fluorescence quantum efficiency and narrow half-peak width, and can be used in various electronic devices with functions such as light emission, display, and lighting to improve device performance.
  • the embodiments of the present application provide the above-mentioned compounds and their salts in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, luminescent electrochemical cells, photovoltaic Applications in converters, light switching devices, image sensors, lasers or photosensitive devices.
  • the above-mentioned compounds can be used as light-emitting materials in the above-mentioned devices.
  • the above-mentioned compounds provided in the embodiments of the present application can be used in organic electroluminescent devices, and can be used as materials for the luminescent layer of organic electroluminescent devices, which can improve the luminous efficiency, luminous stability, color purity, lifespan, etc. of the device.
  • the compounds in the embodiments of the present application have narrow half-peak width, high fluorescence quantum yield, and suitable HOMO and LUMO energy levels, and can be used as doping materials for the emitting layer of organic electroluminescent devices, thereby improving device efficiency.
  • Luminous color purity and device stability; introducing the compounds of the embodiments of the present application as doping materials into the light-emitting layer can play an exciton sensitization role and effectively improve device efficiency and lifespan.
  • the embodiments of the present application provide an electronic device.
  • the electronic device includes the compound described above in the embodiments of the present application.
  • the electronic device may be, for example, an organic electroluminescent device, an organic luminescent field effect transistor, an organic photovoltaic device, a luminescent electrochemical cell, or the like.
  • Figure 1 is a schematic structural diagram of an organic electroluminescent device (OLEDs) 100 provided by an embodiment of the present application.
  • the organic electroluminescent device 100 shown in FIG. 1 includes an anode 10, a cathode 20, and a functional layer 30 located between the anode 10 and the cathode 20.
  • the functional layer 30 includes a light-emitting layer 301.
  • the light-emitting layer 301 includes the above-mentioned compound provided in the embodiment of the present application.
  • the light-emitting layer 301 contains a host material and a doping material (also referred to as a "guest material"), wherein the doping material includes at least one compound described above in the present application.
  • the compound can act as a sensitizing exciton and improve the luminous efficiency of the device; the half-peak width of the compound is narrow, which can improve the purity of the luminescent color of the device and improve the color of the device.
  • the compound has appropriate HOMO energy levels and LUMO energy levels, which can effectively reduce the triplet exciton concentration of the host material and reduce the quenching probability of triplet excitons. Effectively improve the stability and life of the device.
  • the doping material of the light-emitting layer 301 may only include one or more compounds mentioned above in this application; or may include one or more compounds mentioned above in this application and other doping materials at the same time.
  • the other doping materials may be various doping materials available in the field, and may be selected according to actual needs.
  • the host material of the light-emitting layer 301 may include one or more kinds.
  • the host material may be a variety of host materials available in the art, and may be selected according to actual needs.
  • the light-emitting layer 301 includes two host materials.
  • the two host materials can be respectively called a first host material and a second host material. At least one of the first host material and the second host material It is a thermally activated delayed fluorescence (TADF) material.
  • TADF thermally activated delayed fluorescence
  • the host material of the light-emitting layer is composed of two materials. The energy transfer efficiency between it and the above-mentioned compound as a doping material is high, which can fully utilize the luminescent potential of the compound and improve the luminescence of the device. higher efficiency.
  • the constituent materials of the anode 10 and the cathode 20 are conductive materials, which can be independently selected from conductive metals, conductive metal oxides, conductive polymers, etc.
  • the conductive metal may include one or more of magnesium (Mg), aluminum (Al), gold (Au), silver (Ag), platinum (Pt), target (Pd) and other metal elements and their alloys;
  • conductive Metal oxides include but are not limited to indium tin oxide (ITO), indium zinc oxide (IZO), aluminum-doped zinc oxide (AZO), fluorine-doped tin dioxide (FTO), phosphorus-doped tin dioxide (PTO), etc.
  • conductive polymers include but are not limited to polythiophene, polypyrrole, polyaniline, etc.
  • the functional layer 30 also includes a first carrier transport layer 302 located between the anode 10 and the luminescent layer 301 , and a second carrier transport layer 302 located between the cathode 20 and the luminescent layer 301 .
  • the first carrier transport layer 302 may include one or more of a hole injection layer 3021, a hole transport layer 3022, and an electron blocking layer 3023 located between the anode 10 and the light-emitting layer 301.
  • the hole injection layer 3021 is located between the anode 10 and the hole transport layer 3022
  • the electron blocking layer 3023 is located between the light emitting layer 301 and the hole transport layer 3022.
  • the second carrier transport layer 303 may include one or more of an electron injection layer 3031, an electron transport layer 3032, and a hole blocking layer 3033 located between the cathode 20 and the light-emitting layer 301.
  • the electron injection layer 3031 is located on the cathode 20 and the electron transport layer 3032
  • the hole blocking layer 3033 is located between the cathode 20 and the hole transport layer 3022.
  • the organic electroluminescent device 100 includes an anode 10 , a hole injection layer 3021 , a hole transport layer 3022 , an electron blocking layer 3023 , a light emitting layer 301 , and a hole blocking layer 3033 arranged in sequence.
  • the functional layer 30 may also include a stacked structure of "light-emitting layer 301/electron transport layer 3032" in sequence along the direction from the anode 10 to the cathode 20, or a stacked structure of "light-emitting layer 301/electron injection layer 3031", or include The stacked structure of "hole injection layer 3021/light-emitting layer 301/electron transport layer 3032", or the stacked structure of "hole injection layer 3021/light-emitting layer 301/electron injection layer 3031", or the stacked structure of "hole transport layer 3022” /Light-emitting layer 301/electron transport layer 3032", or a laminate structure including "hole injection layer 3021/hole transport layer 3022/light-emitting layer 301/electron transport layer 3032", or including "hole injection layer 3021/hole transport layer 3022/light-emitting layer 301/electron transport layer 3032", or including "hole injection layer 3021/hole transport layer 3022/light-emitting layer 301/elec
  • the organic electroluminescent device 100 may also have a substrate 40 (as shown in FIG. 1 ).
  • the substrate 40 may be located on the side of the anode 10 away from the functional layer 30 (as shown in FIG. 1 ).
  • the organic electroluminescent device 100 is a bottom-emitting device.
  • the substrate 40 may also be located on the side of the cathode 20 away from the functional layer 30.
  • the organic electroluminescent device 100 is a top-emitting device.
  • the top-emitting device includes the cathode 20, the functional layer 30 and the anode 10 which are sequentially arranged on the substrate 40.
  • the substrate 40 can serve as a support for the entire organic electroluminescent device 100, and its material can be quartz, glass, elemental silicon, metal, plastic, etc. In some embodiments, substrate 40 is light-transparent glass or plastic.
  • the shape of the substrate 40 may be determined according to specific application scenarios, and may be formed into a plate shape, a film shape, a sheet shape, etc., for example.
  • the thickness of the substrate 40 is not particularly limited.
  • the physical vapor deposition method can include vacuum evaporation methods (such as resistance evaporation source evaporation method, electron beam evaporation source evaporation method, pulse laser deposition method, etc.), sputtering methods (such as magnetron sputtering method), etc.
  • One or more coating methods may include solution spin coating, dip coating, blade coating, spray coating, roller coating, inkjet printing, screen printing, etc.
  • the anode 10 and the cathode 20 can be prepared by vacuum evaporation, and each layer of the functional layer 30 can be prepared by vacuum evaporation or coating.
  • the anode 10 can be formed on the substrate 40 first, and then the functional layer 30 including the light-emitting layer 301 is sequentially formed on the anode 10, and then the cathode is formed on the functional layer 30. 20.
  • the cathode 20 and the functional layer 30 including the light-emitting layer 301 may be sequentially formed on the substrate 40 , and then the anode 10 may be formed on the functional layer 30 .
  • an embodiment of the present application further provides a display device 200 .
  • the display device 200 includes the electronic device described above in the embodiment of the present application, and may specifically include the above-mentioned organic electroluminescent device 100 .
  • the display device 200 can be a mobile phone, a tablet computer, a notebook computer, a wearable device (such as a smart watch, a smart bracelet, etc.), a television, a digital camera, a camcorder, a player, a micro-display device (such as smart glasses, virtual reality (VR) equipment, augmented reality (AR) equipment, telephones, printers, vehicles, household appliances, billboards, information boards, car central control screens, etc.
  • An embodiment of the present application also provides a lighting device, which includes the electronic device described above in the embodiment of the present application. Specifically, it may include the above-mentioned organic electroluminescent device 100.
  • Illuminating devices can include automobile taillights, automobile headlights, automobile fog lamps, indoor lighting devices (including commercial or household, etc., such as table lamps, ceiling lights, etc.), outdoor lighting devices (such as street lamps), and liquid crystals using organic electroluminescent devices. Backlight of display device, etc.
  • an embodiment of the present application further provides an electronic device 300 .
  • the electronic device 300 includes the above-mentioned display device 200 in the embodiment of the present application.
  • the electronic device 300 can be a mobile phone, a tablet computer, a notebook computer, a wearable device (such as a smart watch, a smart bracelet, etc.), a television, a digital camera, a camcorder, a player, a micro-display device (such as smart glasses, virtual reality) (Virtual Reality, VR) equipment, augmented reality (Augmented Reality, AR) equipment, telephones, printers, vehicles, household appliances, billboards, information boards, car central control screens and other electronic products with display functions.
  • virtual reality Virtual Reality
  • AR Augmented Reality
  • Figure 4 is an LC-MS (liquid chromatography-mass spectrometry) spectrum of compound 4 prepared in Example 1 of the present application.
  • MS measured value: 849.45 [M + H] + , theoretical value: 848.45.
  • Figures 5 and 6 are respectively the hydrogen nuclear magnetic resonance spectrum and the carbon nuclear magnetic resonance spectrum of compound 4 prepared in Example 1 of the present application.
  • FIG. 7 is the ultraviolet absorption spectrum and fluorescence spectrum of compound 4 in Example 1 of the present application.
  • the absorption peak is tested by a double-beam UV-visible spectrophotometer; the luminescence peak and FWHM (width at half maximum) are measured by a fluorescence spectrometer in the film state; Stokes shift refers to the corresponding fluorescence spectrum.
  • the red shift of the absorption spectrum is calculated by subtracting the peak absorption peak from the peak emission peak.
  • the luminescence peak and FWHM of the comparative example were obtained by purchasing commercial Ir(ppy) 3 test film.
  • compound 4, compound 32, and compound 139 have small Stokes shifts (only 22 nm), indicating that the materials can be well sensitized by sensitizing materials that emit visible light.
  • the commercial phosphorescent material Ir(ppy) 3 (full name: fac-Tris(2-phenylpyridine)iridium(III)) as a comparative example, it can be seen that the Stokes shift of the compounds in the embodiments of the present application is much smaller than
  • the commercial phosphorescent material Ir(ppy) 3 shows that the compound provided in this application can not only prepare devices through ordinary doping systems, but also use sensitization to prepare devices.
  • the comparative example does not have such advantages.
  • the compound spectrum FWHM is much narrower than that of the Ir(ppy) 3 material in the comparative example, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device.
  • an organic electroluminescent device as shown in Figure 12, the device includes a substrate 40 (specifically, a transparent glass substrate), an ITO anode 10 (thickness: 150 nm), and a first hole transport layer laminated on the substrate 40 in sequence.
  • Layer 3022a TAPC material, thickness is 30nm
  • second hole transport layer 3022b TCTA material, thickness is 10nm
  • electron blocking layer 3023 mCP material, thickness is 10nm
  • light-emitting layer 301 PF as host material
  • DACT -II is used as the thermally delayed fluorescent sensitizer material
  • compound 4 is used as the fluorescent doping material
  • the mass ratio of the host material, sensitizer material, and compound 4 is 68:30:2
  • the film thickness of the light-emitting layer is 20nm
  • the hole blocking layer 3033 PPF material, thickness is 5nm
  • electron transport layer 3032 BPhen material, thickness is 40nm
  • electron injection layer 3031 LiF layer, thickness is 1nm
  • the preparation process of the above-mentioned OLED light-emitting device is as follows: the ITO anode 10 is washed, that is, washed with a cleaning agent, washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO.
  • a vacuum evaporation device was used to evaporate TAPC with a film thickness of 30 nm as the first hole transport layer 3022a.
  • TCTA with a thickness of 10 nm is evaporated as the second hole transport layer 3022b.
  • mCP with a thickness of 10 nm was evaporated as the electron blocking layer 3023.
  • the luminescent layer 301 of the OLED light-emitting device is produced, using PPF host material, DACT-II as the thermally delayed fluorescent sensitizer material, Compound 4 as the fluorescent doping material, host material, and sensitizer material.
  • compound 4 is mixed according to the mass ratio of 68:30:2, and the film thickness of the luminescent layer 301 is 20nm.
  • the above-mentioned light-emitting layer 301 continue to vacuum evaporate PPF to a film thickness of 5 nm. This layer is the hole blocking layer 3033.
  • the luminescent layer 301 uses PPF host material, DACT-II as the thermally delayed fluorescence sensitizer material, and Compound 4 as the fluorescent doping material.
  • the mass ratio of the host material, sensitizer material, and Compound 4 is 78:20. :2.
  • Device Comparative Example 1 The only difference between Device Comparative Example 1 and Device Example 1 is that the light-emitting layer 301 is mixed with CBP and Ir(ppy) 3 at a mass ratio of 97:3.
  • FIG. 13 is the luminescence spectrum diagram of the device of Device Embodiment 1 and Device Example 2 of the present application
  • Figure 14 is the current density-voltage-brightness diagram of the device of Device Embodiment 1 and Device Example 2 of the present application
  • Figure 15 It is the brightness-external quantum efficiency diagram of the device of Device Example 1 and Device Example 2 of the present application.
  • the lighting voltage of the device can be obtained from Figure 14, and the external quantum efficiency of the device can be obtained from Figure 15.
  • the turn-on voltage, external quantum efficiency, and luminescence peak of the devices in Table 2 are tested using the IVL (current-voltage-brightness) test system; the turn-on voltage is tested at a brightness of 1cd/ m2 , and the external quantum efficiency and luminescence peak are both at Tested at 1000cd/ m2 .
  • the external quantum efficiency of the OLED device prepared using the compound of the embodiment of the present application is improved, and the half-height bandwidth of the device luminescence peak is greatly increased. decreased, improving the color purity of the device.
  • the compound provided in the embodiment of the present application has a relatively high and narrow spectrum FWHM, which can effectively improve the color gamut of the device, improve the luminous efficiency of the device, and also improve the luminescence stability.
  • the OLED device prepared using the compounds of the embodiments of the present application has a lower lighting voltage.

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  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composé, le composé étant un polymère ayant une structure telle que représentée dans la formule (I) : Dans la formule, M2 et M3 représentent chacun un cycle aromatique substitué ou non substitué, un cycle hétéroaromatique substitué ou non substitué, ou un cycle aliphatique substitué ou non substitué ; Z est C(R1) ; Y est NR2, O, S ou SE ; R1 et R2 sont, à chaque occurrence, indépendamment choisis parmi un atome d'hydrogène, un atome de deutérium, un atome de tritium, un atome d'halogène, un groupe alkyle substitué ou non substitué, un groupe cycloalkyle substitué ou non substitué, un groupe hétérocycloalkyle substitué ou non substitué, etc ; et R1 adjacent peut être relié pour former un cycle. Le composé a une bonne efficacité d'émission de lumière, et peut être utilisé dans un dispositif électroluminescent pour améliorer les performances du dispositif électroluminescent.
PCT/CN2023/094605 2022-05-18 2023-05-16 Composé et son utilisation WO2023221997A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020135687A1 (fr) * 2018-12-29 2020-07-02 江苏三月光电科技有限公司 Composé contenant du bore, son procédé de préparation et son utilisation
US20210126196A1 (en) * 2019-10-28 2021-04-29 Samsung Display Co., Ltd. Compound and light-emitting device including the same
CN114181239A (zh) * 2021-12-27 2022-03-15 中国科学院长春应用化学研究所 含有萘环的硼杂或磷杂稠环化合物及其制备方法和发光器件
CN114195810A (zh) * 2021-12-27 2022-03-18 中国科学院长春应用化学研究所 一种硼杂或磷杂稠环化合物及其制法和发光器件
CN114213441A (zh) * 2021-12-27 2022-03-22 中国科学院长春应用化学研究所 硼杂或磷杂稠环化合物及其制备方法和发光器件

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020135687A1 (fr) * 2018-12-29 2020-07-02 江苏三月光电科技有限公司 Composé contenant du bore, son procédé de préparation et son utilisation
US20210126196A1 (en) * 2019-10-28 2021-04-29 Samsung Display Co., Ltd. Compound and light-emitting device including the same
CN114181239A (zh) * 2021-12-27 2022-03-15 中国科学院长春应用化学研究所 含有萘环的硼杂或磷杂稠环化合物及其制备方法和发光器件
CN114195810A (zh) * 2021-12-27 2022-03-18 中国科学院长春应用化学研究所 一种硼杂或磷杂稠环化合物及其制法和发光器件
CN114213441A (zh) * 2021-12-27 2022-03-22 中国科学院长春应用化学研究所 硼杂或磷杂稠环化合物及其制备方法和发光器件

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