WO2023221997A1 - Compound and use thereof - Google Patents

Compound and use thereof 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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French (fr)
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/en

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    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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    • C07F7/02—Silicon compounds
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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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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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
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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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Abstract

Provided is a compound, the compound being a polymer having a structure as shown in formula (I): < img file ='form CN2023094605-ISRE-I000001 JPG "he =" 32.80 "img-content =" drawing "img-format =" jpg "in line =" yes "orientation =" portraitit "wi =" 49.74 "/>, wherein M2 and M3 are individually a substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring, or a substituted or unsubstituted aliphatic ring; Z is C(R1); Y is NR2, O, S, or SE; R1 and R2 are, at each occurrence, 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 group, etc.; and adjacent R1 may be connected to form a ring. The compound has a good light-emitting performance, and can be used in a light-emitting device to improve the performance of the light-emitting device.

Description

化合物及其应用Compounds and their applications
本申请要求于2022年5月18日提交中国专利局、申请号为202210539150.4、申请名称为“化合物及其应用”的中国专利申请的优先权，其全部内容通过引用结合在本申请中。This application claims priority to the Chinese patent application filed with the China Patent Office on May 18, 2022, with application number 202210539150.4 and application title "Compounds and Applications thereof", the entire content of which is incorporated into this application by reference.
技术领域Technical field
本申请涉及有机发光材料技术领域，特别是涉及一种化合物及其应用。The present application relates to the technical field of organic light-emitting materials, and in particular to a compound and its application.
背景技术Background technique
有机发光材料发光性能较好，可调性好，分子设计相对比较灵活，且可以涂覆至各种基材上成膜，因而被广泛应用于有机电致发光器件(Organic Light Emission Diodes，OLEDs)、有机发光场效应晶体管、有机光伏器件、发光电化学电池、光电转换器、开光器件、图像传感器、激光器、感光器件、生物成像设备、涂料、有机激光设备等各领域中。其中，有机电致发光器件是一种以有机发光材料为发光材料，能把施加的电能转化为光能的能量转化装置。它因具有亮度高、响应快、视角宽、可柔性化等特点而在显示、照明等领域有着广泛应用。然而随着人们对显示装置显示效果要求的提高，相应对OLEDs发光材料也提出了更高的要求，如高效、稳定、高发光色纯度等。因此，有必要开发新的有机发光材料以满足OLEDs日益发展的需求。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. It is widely used in display, lighting and other fields because of its characteristics such as high brightness, fast response, wide viewing angle, and flexibility. However, as people's requirements for display effects of display devices increase, higher requirements are also put forward for OLEDs luminescent materials, such as high efficiency, stability, and high luminous color purity. Therefore, it is necessary to develop new organic light-emitting materials to meet the growing needs of OLEDs.
发明内容Contents of the invention
鉴于此，本申请实施例提供了一种化合物，该化合物具有良好的发光性能，能够提升发光器件性能。In view of this, embodiments of the present application provide a compound that has good luminescent properties and can improve the performance of light-emitting devices.
具体地，本申请实施例第一方面提供一种化合物，所述化合物为式(一)所示结构的多聚体：
Specifically, the first aspect of the embodiments of the present application provides a compound, which is a polymer with a structure shown in formula (1):
其中，M2、M3分别为取代或未取代的芳环、取代或未取代的杂芳环、或取代或未取代的脂肪环；Z为C(R1)，Y为NR2、O、S或Se；R1、R2每次出现独立地选自氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的杂环烯基、取代或未取代的炔基、取代或未取代的环炔基、取代或未取代的杂环炔基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的烷基胺基、取代或未取代的芳胺基、取代或未取代的杂芳胺基、取代或未取代的硼烷基、取代或未取代的硅烷基、取代或未取代的芳香硅基、或除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团，相邻的R1可连接成 环。Among them, 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 cycloalkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted hetero Aryloxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted borane group, substituted or unsubstituted silyl group, Substituted or unsubstituted aromatic silicon group, or C 1 -C 18 electron-withdrawing group containing at least one heteroatom among O, N, S, B, P, F other than the above groups, adjacent R 1 can be connected to ring.
本申请实施例提供的化合物为式(一)所示结构的多聚体，这样化合物分子结构中包含两个或两个以上式(一)所示结构，使得化合物具有良好的发光性能，且易于合成。具体地，化合物以由硼原子、Y基团和萘环等构成的稠环结构为骨架中心，该稠环结构骨架中心可以产生良好的共振效应，共振面积大，共振效应强，且该稠环结构电稳定性高；同时该稠环结构骨架中心为刚性骨架结构，能够有效降低其激发态结构的驰豫程度，从而可使该化合物获得较高荧光量子产率，较窄的半峰宽(FWHM，Full Width at Half Maxima)，以及合适的HOMO(Highest Occupied Molecular Orbital，最高占据分子轨道)和LUMO(Lowest Unoccupied Molecular Orbital，最低未占分子轨道)能级。本申请实施例上述的化合物结构稳定性高、电稳定性高、荧光量子产率高、半峰宽窄，作为发光材料应用于发光器件中，可以提高器件效率、发光色纯度和器件稳定性。本申请实施方式中，通过对稠环结构骨架中心引入各种取代基，可以进一步实现化合物的发光峰位置等的调节，获得更多不同发光颜色(如红光、绿光、蓝光)、不同发光行为(窄光谱、较小斯托克斯位移、高色纯度)的化合物，扩大应用范围。The compound provided in the embodiments of the present application is a polymer with a structure represented by formula (1). In this way, 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. Specifically, 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. 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. In the embodiments of the present application, by introducing various substituents into the center of the fused ring structure skeleton, 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 (narrow spectrum, smaller Stokes shift, high color purity) expand the scope of applications.
本申请实施方式中，所述化合物为2-6个所述式(一)所示的结构的多聚体。不同量的式(一)所示的结构可以获得更多种不同的化合物。In the embodiment of the present application, 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).
本申请实施方式中，所述化合物具有式(I)至式(X)所示的任意一种结构通式：

In the embodiment of the present application, the compound has any general structural formula represented by formula (I) to formula (X):

式(I)至式(X)中，Z为C(R1)，Y为NR2、O、S或Se；R1、R2每次出现独立地选自氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的杂环烯基、取代或未取代的炔基、取代或未取代的环炔基、取代或未取代的杂环炔基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的烷基胺基、取代或未取代的芳胺基、取代或未取代的杂芳胺基、取代或未取代的硼烷基、取代或未取代的硅烷基、取代或未取代的芳香硅基、或除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团，相邻的R1可连接成环，R2可与邻近的R1连接成环。上述式(I)至式(X)的化合物发光性能好，且易于制备，有利于实现量产。In 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 arylamine group, substituted Or unsubstituted heteroarylamino group, substituted or unsubstituted borane group, substituted or unsubstituted silyl group, substituted or unsubstituted aromatic silicon group, or other than the above groups containing O, N, S, B , the C 1 -C 18 electron-withdrawing group of at least one heteroatom in P or F, adjacent R 1 can be connected to form a ring, and R 2 can be connected to adjacent R 1 to form a ring. The compounds of the above formulas (I) to (X) have good luminescence properties and are easy to prepare, which is beneficial to mass production.
本申请实施方式中，所述取代的烷基、取代的环烷基、取代的杂环烷基、取代的烯基、取代的环烯基、取代的杂环烯基、取代的炔基、取代的环炔基、取代的杂环炔基、取代的烷氧基、取代的芳氧基、取代的芳基、取代的杂芳基、取代的杂芳氧基、取代的烷基胺基、取代的芳胺基、取代的杂芳胺基、取代的硼烷基、取代的硅烷基、取代的芳香硅基中的取代基包括氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基中的一种或多种。不同取代基的选择可以使化合物种类更丰富，获得某些性能稍有差异的化合物产品，更好地实现应用。In the embodiment of the present application, the substituted alkyl group, substituted cycloalkyl group, substituted heterocycloalkyl group, substituted alkenyl group, substituted cycloalkenyl group, substituted heterocycloalkenyl group, substituted alkynyl group, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted alkoxy, substituted aryloxy, substituted aryl, substituted heteroaryl, substituted heteroaryloxy, substituted alkylamino, substituted 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 cycloalkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, substituted or one or more unsubstituted heteroaryl groups. The selection of different substituents can enrich the types of compounds, obtain certain compound products with slightly different properties, and better realize applications.
本申请实施方式中，所述取代或未取代的烷基为取代或未取代C1-C30烷基；所述取代或未取代的环烷基为取代或未取代C3-C30环烷基；所述取代或未取代的杂环烷基为取代或未取代C2-C30杂环烷基；所述取代或未取代的烯基为取代或未取代C2-C30烯基；所述取代或未取代的环烯基为取代或未取代C3-C10环烯基；所述取代或未取代的杂环烯基为取代或未取代C2-C10杂环烯基；所述取代或未取代的炔基为取代或未取代C2-C30炔基；所述取代或未取代的环炔基为取代或未取代C6-C10环炔基；所述取代或未取代的杂环炔基为取代或未取代C5-C10杂环炔基；所述取代或未取代的烷氧基为取代或未取代C1-C30烷氧基；所述取代或未取代的芳氧基为取代或未取代C6-C30芳氧基；所述取代或未取代的芳基为取代或未取代C6-C30芳基；所述取代或未取代的杂芳基为取代或未取代C3-C30杂芳基；所述取代或未取代的杂芳氧基为取代或未取代C3-C30杂芳氧基；所述取代或未取代的烷基胺基为取代或未取代C1-C30烷基胺基；所述取代或未取代的芳胺基为取代或未取代C6-C30芳胺基；所述取代或未取代的杂芳胺基为取代或未取代C3-C30杂芳胺基。将各基团的碳原子数控制在一定的数量，能够使原料更易得，制备过程更可控。In the embodiment of the present application, 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. base; 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 -C 10 cycloalkynyl group; the substituted or The unsubstituted heterocyclic alkynyl group is a substituted or unsubstituted C 5 -C 10 heterocyclic alkynyl group; the substituted or unsubstituted alkoxy group is a substituted or unsubstituted C 1 -C 30 alkoxy group; the substituted or The unsubstituted aryloxy group is a substituted or unsubstituted C 6 -C 30 aryloxy group; the substituted or unsubstituted aryl group is a substituted or unsubstituted C 6 -C 30 aryl group; the substituted or unsubstituted hetero The aryl group is a substituted or unsubstituted C 3 -C 30 heteroaryl group; the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C 3 -C 30 heteroaryloxy group; the substituted or unsubstituted alkyl The amino group is a substituted or unsubstituted C 1 -C 30 alkylamine group; the substituted or unsubstituted arylamine group is a substituted or unsubstituted C 6 -C 30 arylamine group; the substituted or unsubstituted hetero The arylamine group is a substituted or unsubstituted C 3 -C 30 heteroarylamino group. Controlling the number of carbon atoms in each group to a certain number can make the raw materials more accessible and the preparation process more controllable.
本申请实施方式中，所述除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团包括取代或未取代的酰亚胺基、取代或未取代的酰胺基、氰基、硝基 或羟基。In the embodiment of the present application, 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.
本申请实施方式中，所述R1、R2每次出现独立地为氢原子、氘原子、氚原子、卤素原子、氰基、金刚烷基、甲基、氘代甲基、氚代甲基、氟代丙基、三氟甲基、乙基、氘代乙基、氚代乙基、异丙基、氘代异丙基、氚代异丙基、叔丁基、氘代叔丁基、氚代叔丁基、苯基取代的叔丁基、环戊基、氘代环戊基、氚代环戊基、甲基取代的环戊基、环己基、苯基、氘代苯基、氚代苯基、二联苯基、氘代二联苯基、氚代二联苯基、三联苯基、氘代三联苯基、氚代三联苯基、二苯醚基、甲基取代的二苯醚基、萘基、蒽基、菲基、芘基、吡啶基、苯基取代的吡啶基、喹啉基、呋喃基、噻吩基、苯并呋喃基、二苯并呋喃基、叔丁基取代的二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、叔丁基取代的咔唑基、叔丁基取代的N-咔唑基苯基、9,9-二甲基芴基、螺芴基、甲基取代的苯基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、二联苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、苯基取代的氨基、叔丁基苯取代的氨基、叔丁基取代的二苯并呋喃基、苯基取代的叔丁基、氧杂蒽酮基、三嗪基、苯基取代的三嗪基、硼烷基、苯基取代的硼烷基、甲氧基或叔丁氧基。上述的各基团有利于获得良好发光性能的化合物，且能够使化合物易于实现制备。In the embodiment of the present application, 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, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, phenyl substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, tert-butyl substituted Dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted carbazolyl, tert-butyl-substituted N-carbazolylphenyl, 9,9 -Dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, diphenyl, methyl-substituted Diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted benzene base, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted diphenyl, deuterated ethyl substituted diphenyl, deuterated isopropyl substituted Diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl , xanthonyl, triazinyl, phenyl-substituted triazinyl, boryl, phenyl-substituted boryl, methoxy or tert-butoxy. Each of the above groups is beneficial to obtaining compounds with good luminescent properties, and can make the compounds easy to prepare.
本申请实施方式中，相邻的所述R1连接成环时，所形成的环结构包括式(a)至式(i)所示的任意一种：
In the embodiment of the present application, when the adjacent R 1s are connected to form a ring, the ring structure formed includes any of the formulas (a) to (i):
式(a)至式(i)中，*标记的位置为连接位置，式(a)至式(i)的结构通过*标记的位置以并环方式进行连接。相邻R1连接成上述的环结构，不仅可以使化合物种类更丰富，更好地实现应用，且可以使化合物获得良好发光性能，易于实现制备。In 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.
本申请实施方式中，所述R2与邻近的所述R1连接成环时，所形成的环结构包括式(A)至式(D)所示的结构：
In the embodiment of the present application, when the R 2 and the adjacent R 1 are connected to form a ring, the ring structure formed includes the structures represented by formulas (A) to (D):
式(A)中R5为氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基，n为0至4的整数；式(A)至式(D)中，*标记的位置为连接位置，式(A)至式(D)的结构通过*标记的位置以并环方式进行连接。R2与邻近的所述R1连接成上述的环 结构，不仅可以使化合物种类更丰富，更好地实现应用，且可以使化合物获得良好发光性能，易于实现制备。In the formula (A), 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), the positions marked with * 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.
本申请实施方式中，所述化合物包括结构式如式(1)-(268)所示的化合物中的任一种：















In the embodiment of the present application, the compound includes any one of the compounds with structural formulas such as formulas (1)-(268):















本申请实施例第二方面提供第一方面所述的化合物及其盐在电致发光器件、有机发光场效应晶体管、有机光伏器件、发光电化学电池、光电转换器、开光器件、图像传感器、激光器、感光器件、生物成像设备、涂料、有机激光设备中的应用。本申请实施例的化合物具有良好的发光性能，能够提升发光器件性能。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.
本申请实施例第三方面提供一种发光层，所述发光层包括第一方面所述的化合物。本申请实施例的化合物具有良好的发光性能，能够提升发光器件性能。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.
本申请实施方式中，所述发光层包括主体材料和掺杂材料，所述掺杂材料包括所述化合物。本申请实施例的化合物具有较小的斯托克位移，能够作为掺杂材料较好地敏化发射可见光的主体材料。In the embodiment of the present application, the light-emitting layer includes a host material and a doping material, and 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.
本申请实施例第四方面提供一种电子器件，所述电子器件包括第一方面所述的化合物；或者包括第三方面所述的发光层。本申请实施例的化合物具有良好的发光性能，能够提升发光器件性能。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.
本申请实施方式中，所述电子器件包括阴极和阳极，以及位于所述阴极和所述阳极之间的功能层，所述功能层包括所述化合物。In an embodiment of the present application, 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.
本申请实施方式中，所述电子器件包括电致发光器件、有机发光场效应晶体管、有机光伏器件或发光电化学电池。In the embodiment of the present application, the electronic device includes an electroluminescent device, an organic light-emitting field effect transistor, an organic photovoltaic device or a luminescent electrochemical cell.
本申请实施例第五方面提供一种显示装置，所述显示装置包括第四方面所述的电子器件；或者包括第三方面所述的发光层。本申请实施例的化合物具有良好的发光性能，有利于提高显示装置的显示效果。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.
本申请实施例还提供一种电子设备，其特征在于，所述电子设备包括第五方面所述的显示装置；或者包括第四方面所述的电子器件。本申请实施例的化合物具有良好的发光性能，有利于提高电子设备的显示效果，提高电子设备的市场竞争力。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.
本申请实施例还提供一种照明装置，其特征在于，所述照明装置包括第四方面所述的电子器件；或者包括第三方面所述的发光层。本申请实施例的化合物具有良好的发光性能，有 利于提高照明装置的发光效果，提高照明装置的市场竞争力。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.
附图说明Description of the drawings
图1为本申请实施例提供的有机电致发光器件100的结构示意图；Figure 1 is a schematic structural diagram of an organic electroluminescent device 100 provided by an embodiment of the present application;
图2为本申请实施例提供的显示装置200的结构示意图；Figure 2 is a schematic structural diagram of a display device 200 provided by an embodiment of the present application;
图3为本申请实施例提供的电子设备300的结构示意图；Figure 3 is a schematic structural diagram of an electronic device 300 provided by an embodiment of the present application;
图4为本申请实施例1制备的化合物4的高分辨质谱图；Figure 4 is a high-resolution mass spectrum of compound 4 prepared in Example 1 of the present application;
图5和图6分别为本申请实施例1制备的化合物4的核磁共振氢谱和核磁共振碳谱；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;
图7为本申请实施例1中化合物4的紫外吸收光谱和荧光光谱；Figure 7 is the ultraviolet absorption spectrum and fluorescence spectrum of compound 4 in Example 1 of the present application;
图8为本申请实施例2制备的化合物32的核磁共振氢谱；Figure 8 is a hydrogen nuclear magnetic resonance spectrum of compound 32 prepared in Example 2 of the present application;
图9为本申请实施例2中化合物32的荧光光谱；Figure 9 is the fluorescence spectrum of compound 32 in Example 2 of the present application;
图10为本申请实施例3制备的化合物139的核磁共振氢谱；Figure 10 is the hydrogen nuclear magnetic resonance spectrum of compound 139 prepared in Example 3 of the present application;
图11为本申请实施例3中化合物139的紫外吸收光谱和荧光光谱；Figure 11 is the ultraviolet absorption spectrum and fluorescence spectrum of compound 139 in Example 3 of the present application;
图12为器件实施例1的有机电致发光器件100的结构示意图；Figure 12 is a schematic structural diagram of the organic electroluminescent device 100 of Device Embodiment 1;
图13为本申请器件实施例1和器件实施例2的器件的发光光谱图；Figure 13 is a luminescence spectrum diagram of the device of Device Embodiment 1 and Device Embodiment 2 of the present application;
图14为本申请器件实施例1和器件实施例2的器件的电流密度-电压-亮度图；Figure 14 is a current density-voltage-brightness diagram of the devices of Device Embodiment 1 and Device Embodiment 2 of the present application;
图15为本申请器件实施例1和器件实施例2的器件的亮度-外量子效率图。Figure 15 is a brightness-external quantum efficiency diagram of the devices of Device Example 1 and Device Example 2 of the present application.
具体实施方式Detailed ways
下面将结合本申请实施例中的附图，对本申请实施例进行说明。The embodiments of the present application will be described below with reference to the drawings in the embodiments of the present application.
参见图1，图1为本申请实施例提供的有机电致发光器件(OLEDs)100的结构示意图。图1所示的有机电致发光器件100包括阳极10、阴极20、以及位于阳极10和阴极20之间的功能层30，功能层30包括发光层301。在有机电致发光器件100的阳极10与阴极20之间施加一定的电压后，发光层301中的发光材料藉由空穴与电子在发光层301中的再结合受到激发而发光，从而赋予有机电致发光器件100发光功能。其中，随着5G时代的到来，新一代的显示标准对显示技术提出了更高的要求，如发光层301中的发光材料需要具备发光效率高、性质稳定外、发光色纯度高等性能，以满足更高要求的显示标准。为此，本申请实施例提供了一种化合物，该化合物可用于上述发光层301，使有机电致发光器件获得良好的发光性能，且该化合物易于实现制备。Referring to Figure 1, 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. 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. Among them, with the arrival of the 5G era, the new generation of display standards has put forward higher requirements for display technology. For example, 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. To this end, 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.
下面将具体介绍上述化合物，该化合物为含硼有机化合物，该化合物为式(一)所示结构的多聚体：
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):
其中，M2、M3分别为取代或未取代的芳环、取代或未取代的杂芳环、或取代或未取代的脂肪环；Z为C(R1)，Y为NR2、O、S或Se；R1、R2每次出现独立地选自氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环烷 基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的杂环烯基、取代或未取代的炔基、取代或未取代的环炔基、取代或未取代的杂环炔基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的烷基胺基、取代或未取代的芳胺基、取代或未取代的杂芳胺基、取代或未取代的硼烷基、取代或未取代的硅烷基、取代或未取代的芳香硅基、或除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团，相邻的R1可连接成环。Among them, 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 cycloalkynyl, substituted or unsubstituted Heterocyclic alkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy , substituted or unsubstituted alkylamine group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted borane group, substituted or unsubstituted silyl group, substituted or unsubstituted silyl group Substituted aromatic silicon group, or C 1 -C 18 electron-withdrawing group containing at least one heteroatom among O, N, S, B, P, F other than the above groups, adjacent R 1 can be connected Form a ring.
本申请实施例提供的化合物为式(一)所示结构的多聚体，这样化合物分子结构中包含两个或两个以上式(一)所示结构，由于式(一)所示结构具有包括B原子和Y原子(或基团)的1号环，1号环为硼杂环，且2号环上通过并环方式引入了萘环，同时在M2环、M3环的共同作用下，使得化合物具有良好的发光性能，且易于合成。The compounds provided in the embodiments of the present application are polymers of the structure represented by formula (1). In this way, 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.
本申请实施方式中，式(一)中，M2、M3分别为取代或未取代的芳环、取代或未取代的杂芳环、或取代或未取代的脂肪环；具体地，取代或未取代的芳环可以是取代或未取代的C6-C30芳环，例如取代或未取代的苯环、取代或未取代的萘环、取代或未取代的蒽环、取代或未取代的菲环、取代或未取代的二联苯环、取代或未取代的三联苯环、取代或未取代的联萘环、取代或未取代的芴环、取代或未取代的螺芴环等；取代或未取代的杂芳环可以是取代或未取代的C3-C30杂芳环，例如取代或未取代的吡啶环、取代或未取代的喹啉环、取代或未取代的呋喃环、取代或未取代的噻吩环、取代或未取代的苯并呋喃环、取代或未取代的二苯并呋喃环、取代或未取代的苯并噻吩环、取代或未取代的二苯并噻吩环、取代或未取代的咔唑环、取代或未取代的喹啉环、取代或未取代的三嗪环、取代或未取代的氧杂蒽酮环等；取代或未取代的脂肪环可以是取代或未取代的C2-C30脂肪族环结构，例如，取代或未取代的环戊烷环、取代或未取代的环己烷环、取代或未取代的环戊烯环、取代或未取代的环己烯环等。In the embodiment of the present application, in formula (1), 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, substituted or unsubstituted spirofluorene ring, etc.; substituted Or the unsubstituted heteroaromatic ring may be a substituted or unsubstituted C 3 -C 30 heteroaromatic ring, such as a substituted or unsubstituted pyridine ring, a substituted or unsubstituted quinoline ring, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, substituted or unsubstituted benzofuran ring, substituted or unsubstituted dibenzofuran ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted dibenzothiophene ring, substituted Or unsubstituted carbazole ring, substituted or unsubstituted quinoline ring, substituted or unsubstituted triazine ring, substituted or unsubstituted xanthone ring, etc.; the substituted or unsubstituted aliphatic ring can be substituted or unsubstituted Substituted C 2 -C 30 aliphatic ring structure, for example, substituted or unsubstituted cyclopentane ring, substituted or unsubstituted cyclohexane ring, substituted or unsubstituted cyclopentene ring, substituted or unsubstituted ring Hexene ring etc.
本申请实施方式中，M2、M3中，取代的芳环、取代的杂芳环、取代的脂肪环中的取代基包括氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基、取代或未取代的氨基中的一种或多种。In the embodiment of the present application, in M 2 and M 3 , 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.
本申请一些实施方式中，M2、M3分别为苯环、氘代苯环、氚代苯环、甲基取代的苯环、乙基取代的苯环、异丙基取代的苯环、叔丁基取代的苯环、氘代甲基取代的苯环、氘代乙基取代的苯环、氘代异丙基取代的苯环、氘代叔丁基取代的苯环、氰基取代的苯环、金刚烷基取代的苯环、吡啶基取代的苯环、萘环、氘代萘环、氚代萘环、烷基取代的萘环、氘代烷基取代的萘环、氚代烷基取代的萘环、蒽环、氘代蒽环、氚代蒽环、烷基取代的蒽环、氘代烷基取代的蒽环、氚代烷基取代的蒽环、菲环、氘代菲环、氚代菲环、烷基取代的菲环、氘代烷基取代的菲环、氚代烷基取代的菲环、二联苯环、氘代二联苯环、氚代二联苯环、甲基取代的二联苯环、乙基取代的二联苯环、异丙基取代的二联苯环、叔丁基取代的二联苯环、氘代甲基取代的二联苯环、氘代乙基取代的二联苯环、氘代异丙基取代的二联苯环、氘代叔丁基取代的二联苯环、三联苯环、氘代三联苯环、氚代三联苯环、吡啶环、苯基取代的吡啶环、喹啉环、呋喃环、甲基取代的呋喃环、噻吩环、甲基取代的噻吩环、苯并噻吩环、苯并呋喃环、甲基取代的苯并呋喃环、咔唑环、咔唑基苯环、烷基取代的咔唑基苯环、苯基氨基取代的苯环、烷基苯基氨基取代的苯环、N-苯基咔唑环、苯并呋喃环、二苯并呋喃环、叔丁基取代的二苯并呋喃环、二苯并噻吩环、芴环、烷基取代的芴环、螺芴环、三嗪环、苯基取代的三嗪环、氧杂蒽酮环、环戊烷环、氘代环戊烷环、氚代环戊烷环、甲基取代的环戊烷环、环 己烷环、氘代环己烷环、氚代环己烷环、甲基取代的环己烷环、环戊烯环、氘代环戊烯环、氚代环戊烯环、甲基取代的环戊烯环、环己烯环、氘代环己烯环、氚代环己烯环、或甲基取代的环己烯环等。In some embodiments of the present application, 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. Butyl-substituted benzene ring, deuterated methyl-substituted benzene ring, deuterated ethyl-substituted benzene ring, deuterated isopropyl-substituted benzene ring, deuterated tert-butyl substituted benzene ring, cyano-substituted benzene ring Ring, adamantyl-substituted benzene ring, pyridyl-substituted benzene ring, naphthalene ring, deuterated naphthalene ring, tritiated naphthalene ring, alkyl-substituted naphthalene ring, deuterated alkyl-substituted naphthalene ring, tritiated alkyl group Substituted naphthalene ring, anthracene ring, deuterated anthracene ring, tritiated anthracene ring, alkyl-substituted anthracene ring, deuterated alkyl-substituted anthracene ring, tritiated alkyl-substituted anthracene ring, phenanthrene ring, deuterated phenanthrene ring , tritiated phenanthrene ring, alkyl-substituted phenanthrene ring, deuterated alkyl-substituted phenanthrene ring, tritiated alkyl-substituted phenanthrene ring, biphenyl ring, deuterated biphenyl ring, tritiated biphenyl ring, Methyl-substituted diphenyl ring, ethyl-substituted diphenyl ring, isopropyl-substituted diphenyl ring, tert-butyl-substituted diphenyl ring, deuterated methyl-substituted diphenyl ring, deuterium Ethyl-substituted diphenyl ring, deuterated isopropyl-substituted diphenyl ring, deuterated tert-butyl substituted diphenyl ring, terphenyl ring, deuterated terphenyl ring, tritiated terphenyl ring, Pyridine ring, phenyl-substituted pyridine ring, quinoline ring, furan ring, methyl-substituted furan ring, thiophene ring, methyl-substituted thiophene ring, benzothiophene ring, benzofuran ring, methyl-substituted benzo Furan ring, carbazole ring, carbazolyl benzene ring, alkyl-substituted carbazolyl benzene ring, phenylamino-substituted benzene ring, alkylphenylamino-substituted benzene ring, N-phenylcarbazole ring, benzene Furan ring, dibenzofuran ring, tert-butyl-substituted dibenzofuran ring, dibenzothiophene ring, fluorene ring, alkyl-substituted fluorene ring, spirofluorene ring, triazine ring, phenyl-substituted tris Azine ring, xanthone ring, cyclopentane ring, deuterated cyclopentane ring, tritiated cyclopentane ring, methyl-substituted cyclopentane ring, ring Hexane ring, deuterated cyclohexane ring, tritiated cyclohexane ring, methyl-substituted cyclohexane ring, cyclopentene ring, deuterated cyclopentene ring, tritiated cyclopentene ring, methyl-substituted Cyclopentene ring, cyclohexene ring, deuterated cyclohexene ring, tritiated cyclohexene ring, or methyl-substituted cyclohexene ring, etc.
本申请实施方式中，化合物为2-6个式(一)所示的结构的多聚体，例如，化合物可以是2个、3个、4个、5个或6个式(一)所示的结构的多聚体。In the embodiment of the present application, the compound is a multimer of 2-6 structures represented by formula (1). For example, the compound can be 2, 3, 4, 5 or 6 polymers represented by formula (1). The structure of the polymer.
本申请实施例提供的化合物可以具有多种结构形式，化合物中多个式(一)所示的结构可以是通过不同方式实现连接，具体可以是通过共用某些环结构、或通过某些环结构并环连接、或通过连接基团连接等。例如，一些实施例中，化合物中多个式(一)所示的结构可以是通过共用萘环、共用M2环、共用M3环等连接；一些实施例中，化合物中多个式(一)所示的结构可以是通过1号环并环、M2环并环、2号环并环等实现连接；一些实施例中，化合物中多个式(一)所示的结构可以是通过单键、亚苯基、芳环、芳杂环、脂肪环、或脂杂环等连接基团实现连接。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. 2 ring and ring, etc.; in some embodiments, 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.
本申请一些实施方式中，化合物可以是具有式(I)至式(X)所示的任意一种结构通式：

In some embodiments of the present application, the compound may have any general structural formula represented by formula (I) to formula (X):

式(I)至式(X)中，Z为C(R1)，Y为NR2、O、S或Se；R1、R2每次出现独立地选自氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的杂环烯基、取代或未取代的炔基、取代或未取代的环炔基、取代或未取代的杂环炔基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的烷基胺基、取代或未取代的芳胺基、取代或未取代的杂芳胺基、取代或未取代的硼烷基、取代或未取代的硅烷基、取代或未取代的芳香硅基、或除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团，相邻的R1可连接成环，R2可与邻近的R1连接成环。In 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 arylamine group, substituted Or unsubstituted heteroarylamino group, substituted or unsubstituted borane group, substituted or unsubstituted silyl group, substituted or unsubstituted aromatic silicon group, or other than the above groups containing O, N, S, B , the C 1 -C 18 electron-withdrawing group of at least one heteroatom in P or F, adjacent R 1 can be connected to form a ring, and R 2 can be connected to adjacent R 1 to form a ring.
本申请实施例提供的化合物，其以由硼原子、Y基团和萘环等构成的稠环结构为骨架中心，该稠环结构骨架中心可以产生良好的共振效应，共振面积大，共振效应强，且该稠环结构电稳定性高；同时该稠环结构骨架中心为刚性骨架结构，能够有效降低其激发态结构的驰豫程度，从而可使该化合物获得较高荧光量子产率，较窄的半峰宽(FWHM，Full Width at Half Maxima)，以及合适的HOMO(Highest Occupied Molecular Orbital，最高占据分子轨道)和LUMO(Lowest Unoccupied Molecular Orbital，最低未占分子轨道)能级；另外，本申请实施例化合物斯托克位移小可以对发射可见光的材料起到很好的敏化作用。其中，“半峰宽”是指发光材料电致发光光谱中发光峰高一半处的峰宽度。本申请实施例的化合物可以实现小于30nm的半峰宽。将本申请实施例上述的化合物结构稳定性高、电稳定性高、荧光量子产率高、半峰宽窄，作为发光材料应用于发光器件中，可以提高器件效率、发光色纯度和器件稳定性。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. , and 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. Among them, "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. When 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.
本申请实施方式中，通过对稠环结构骨架中心引入各种取代基，可以进一步实现化合物的发光峰位置等的调节，获得更多不同发光颜色(如红光、绿光、蓝光)、不同发光行为(窄光谱、较小斯托克斯位移、高色纯度)的化合物，扩大应用范围。其中，例如可将化合物的发光位置调至绿光区域，在全彩发光器件中，绿色作为主发光色，提供全屏约60％的亮度，当上述化合物发绿光时，更利于其在OLED-RGB三原色的全彩发光器件及OLED白光照明等领域得到广泛应用。本申请实施例的化合物可通过较简单的合成路径获得，不需要使用丁基锂等危险化学品即可实现合成，适于工业化生产，在OLED照明或者OLED显示领域具有良好的应用效果和产业化前景。In the embodiments of the present application, by introducing various substituents into the center of the fused ring structure skeleton, 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 (narrow spectrum, smaller Stokes shift, high color purity) expand the scope of applications. Among them, for example, the light-emitting position of the compound can be adjusted to the green light area. In a full-color light-emitting device, green is used as the main light-emitting color, providing about 60% of the brightness of the full screen. When 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.
本申请实施方式中，式(I)至式(X)中，Z表示为C(R1)；其中，R1每次出现可以是相同结构的基团或不同结构的基团。即不同位置的Z可以是具有相同结构或者不同结构，具体可以是所有位置的Z均相同，或者所有位置的Z不相同，或者部分位置的Z相同。例如，一些实施例中，式(I)至式(X)中，所有Z均为C(H)，或者一些Z为C(H)，其余的Z为-C(CH3)。In the embodiment of the present application, in Formula (I) to Formula (X), 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 ).
本申请实施方式中，式(I)至式(X)中，Y每次出现时可以是相同结构的基团或不同 结构的基团，即多个Y可以是相同结构的基团或不同结构的基团。其中，当多个Y为相同结构的基团时，可以是多个Y均为O、S、N(R2)、或Se；此时，含硼有机化合物更易合成，且化合物的对称性更高，对称的刚性骨架结构更利于降低该化合物激发态结构的驰豫程度，获得较窄半峰宽。当多个Y为不同结构的基团时，可以是完全不同类型的基团，以化合物中包含两个Y为例，例如可以是其中一个Y为S或O或Se，另一个Y为N(R2)，或者其中一个Y为O，另一个Y为S；也可以是具有不同结构的同一类型基团，例如两个Y均为N(R2)，但R2不相同。式(I)至式(X)中两个Y均含杂原子，更利于与结构式中的两个硼原子产生强的共振效应。In the embodiments of the present application, 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. Among them, 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. When multiple Y are groups with different structures, they can be completely different types of groups. For example, if 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.
本申请实施方式中，上述基团选择中涉及的取代的烷基、取代的环烷基、取代的杂环烷基、取代的烯基、取代的环烯基、取代的杂环烯基、取代的炔基、取代的环炔基、取代的杂环炔基、取代的烷氧基、取代的芳氧基、取代的芳基、取代的杂芳基、取代的杂芳氧基、取代的烷基胺基、取代的芳胺基、取代的杂芳胺基、取代的硼烷基、取代的硅烷基、取代的芳香硅基中的取代基包括氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基中的一种或多种。In the embodiment of the present application, the substituted alkyl group, substituted cycloalkyl group, substituted heterocycloalkyl group, substituted alkenyl group, substituted cycloalkenyl group, substituted heterocycloalkenyl group, substituted Alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted alkoxy, substituted aryloxy, substituted aryl, substituted heteroaryl, substituted heteroaryloxy, substituted alkyl 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 or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted One or more of aryloxy groups, substituted or unsubstituted heteroaryl groups.
本申请实施方式中，杂环烷基、杂环烯基、杂环炔基、杂芳基、杂芳氧基和杂芳胺基中的杂原子可以是选自氧原子、硫原子、氮原子、硒原子中的一种或多种。In the embodiment of the present application, 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.
本申请实施方式中，上述涉及的取代或未取代的烷基为链状烷基，可以是直链烷基，也可以是支链烷基，取代或未取代的烷基可以是取代或未取代C1-C30烷基。一些实施例中，取代或未取代的烷基可以是取代或未取代的C1-C10链状烷基、取代或未取代的C1-C6链状烷基，具体例如可以是取代或未取代的甲基、取代或未取代的乙基、取代或未取代的异丙基、取代或未取代的异丁基、取代或未取代的叔丁基等。取代的烷基中的取代基可以是但不限于是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基。示例性的，取代的烷基可以是氘代甲基、氚代甲基、氟代乙基、氟代丙基、三氟甲基、氘代乙基、氚代乙基、氘代异丙基、氚代异丙基、氘代叔丁基、氚代叔丁基、苯基取代的叔丁基等。In the embodiment of the present application, 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. C 1 -C 30 alkyl. In some embodiments, 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. Unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, etc. 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. Exemplarily, 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.
本申请实施方式中，上述涉及的取代或未取代的环烷基可以是取代或未取代C3-C30环烷基。一些实施例中，取代或未取代的环烷基可以是取代或未取代的C4～C12环烷基、取代或未取代C5～C6环烷基，具体例如可以是取代或未取代的环戊基、取代或未取代的环己基、取代或未取代的金刚烷基等；取代的环烷基中的取代基可以是但不限于氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、烷基、烷氧基。示例性地，取代的环烷基可以是氘代环戊基、氚代环戊基、甲基取代的环戊基等。In the embodiment of the present application, the above-mentioned substituted or unsubstituted cycloalkyl group may be a substituted or unsubstituted C 3 -C 30 cycloalkyl group. In some embodiments, 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. cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, etc.; 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. Illustratively, the substituted cycloalkyl group may be deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, and the like.
本申请实施方式中，上述涉及的取代或未取代的杂环烷基可以是取代或未取代C2-C30杂环烷基。一些实施例中，取代或未取代的杂环烷基可以是取代或未取代C4-C12杂环烷基、取代或未取代C5～C6杂环烷基。示例性地，取代或未取代的杂环烷基可以是取代或未取代氮杂环丙烷、取代或未取代氮杂环丁烷、取代或未取代氮杂环戊烷。In the embodiment of the present application, the above-mentioned substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted C 2 -C 30 heterocycloalkyl group. In some embodiments, 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. Illustratively, the substituted or unsubstituted heterocycloalkyl group may be a substituted or unsubstituted aziridine, a substituted or unsubstituted azetidine, or a substituted or unsubstituted azetidine.
本申请实施方式中，上述涉及的取代或未取代的烯基可以是取代或未取代C2-C30烯基；可以是直链烯基，也可以是支链烯基。一些实施例中，取代或未取代的烯基可以是取代或未取代的C2-C10链状烯基、取代或未取代的C2-C6链状烯基，具体例如可以是取代或未取代的乙烯基、取代或未取代的丙烯基等。取代的烯基中的取代基可以是但不限于是氘原子、氚原 子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基。示例性的，取代的烯基可以是氘代乙烯基、氚代乙烯基、氟代乙烯基、氟代丙烯基等。In the embodiment of the present application, 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. In some embodiments, 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. Unsubstituted vinyl, substituted or unsubstituted propenyl, etc. 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. Exemplarily, the substituted alkenyl group may be deuterated vinyl, tritiated vinyl, fluorovinyl, fluoropropenyl, etc.
本申请实施方式中，上述涉及的取代或未取代的环烯基可以是取代或未取代C3-C10环烯基。一些实施例中，取代或未取代的环烯基可以是取代或未取代的C4-C7环烯基、取代或未取代的C5-C6环烯基，具体例如可以是取代或未取代的环戊烯基、取代或未取代的环己烯基等。取代的环烯基中的取代基可以是但不限于是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基。示例性的，取代的环烯基可以是氟代环戊烯基、氟代环己烯基等。In the embodiment of the present application, the above-mentioned substituted or unsubstituted cycloalkenyl group may be a substituted or unsubstituted C 3 -C 10 cycloalkenyl group. In some embodiments, 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. Substituted cyclopentenyl, substituted or unsubstituted cyclohexenyl, etc. 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. Exemplarily, the substituted cycloalkenyl group may be fluorinated cyclopentenyl, fluorinated cyclohexenyl, etc.
本申请实施方式中，上述涉及的取代或未取代的杂环烯基可以是取代或未取代C2-C10环烯基。一些实施例中，取代或未取代的杂环烯基可以是取代或未取代的C3-C6杂环烯基、取代或未取代的C4-C5杂环烯基，具体例如可以是取代或未取代的氮杂环戊二烯、取代或未取代的氧杂环己烯等。取代的杂环烯基中的取代基可以是但不限于是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基。示例性的，取代的杂环烯基可以是氟代杂环戊二烯基、氟代氧杂环己烯基等。In the embodiment of the present application, the above-mentioned substituted or unsubstituted heterocyclic alkenyl group may be a substituted or unsubstituted C 2 -C 10 cycloalkenyl group. In some embodiments, 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. Substituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted aryloxy, substituted or unsubstituted heteroaryl. Exemplarily, the substituted heterocycloalkenyl group may be fluorocyclopentadienyl, fluorooxacyclohexenyl, etc.
本申请实施方式中，取代或未取代的炔基可以是取代或未取代C2-C30炔基；可以是直链炔基，也可以是支链炔基。一些实施例中，取代或未取代的炔基可以是取代或未取代的C2-C10链状炔基、取代或未取代的C2-C6链状炔基，具体例如可以是取代或未取代的乙炔基、取代或未取代的丙炔基等。取代的炔基中的取代基可以是但不限于是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基。示例性的，取代的炔基可以是氘代乙炔基、氚代乙炔基、氟代乙炔基、氟代丙炔基等。In the embodiment of the present application, 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. In some embodiments, 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. Exemplarily, the substituted alkynyl group may be deuterated ethynyl, tritiated ethynyl, fluoroethynyl, fluoropropynyl, etc.
本申请实施方式中，取代或未取代的环炔基可以是取代或未取代C6-C10环炔基。取代或未取代的杂环炔基可以是取代或未取代C5-C10杂环炔基。In the embodiment of the present application, 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.
本申请实施方式中，上述涉及的取代或未取代的烷氧基可以是取代或未取代C1-C30烷氧基，可以是直链烷氧基，也可以是支链烷氧基；一些实施例中，取代或未取代的烷氧基可以是取代或未取代的C1-20烷氧基、C1-C10烷氧基、C1-C6烷氧基。作为示例，取代或未取代的烷氧基可以是取代或未取代的甲氧基(-OCH3)、取代或未取代的乙氧基(-OCH2CH3)、取代或未取代的叔丁氧基等。取代的烷氧基中的取代基可以是但不限于氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、烷基、烷氧基、环烷基等。In the embodiment of the present application, 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. As examples, 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.
本申请实施方式中，上述涉及的取代或未取代的芳基可以是取代或未取代C6-C30芳基；取代或未取代的芳基可以是取代或未取代的C6-C30芳基，芳基可以是单环芳基或多环芳基。一些实施例中，取代或未取代的芳基可以是取代或未取代的C6-C20芳基、取代或未取代的C6-C12芳基。其中，取代的芳基中的取代基可以是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基以及取代或未取代的烷基、环烷基、烷氧基、芳基、芳氧基、杂芳基等。取代或未取代的单环芳基例如可以是苯基、氘代苯基、氚代苯基、甲基取代的苯基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基等。其中，多环芳基可以是稠环型或 非稠环型(如联苯类)。具体地，联苯类的取代或未取代的多环芳基可以但不限于是取代或未取代的二联苯基、三联苯基、二苯醚基(通过氧原子连接的两个苯环)。其中，示例性地，取代的多环芳基可以是氘代二联苯基、氚代二联苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、氘代三联苯基、氚代三联苯基、甲基取代的二苯醚基等。稠环型的取代或未取代的多环芳基可以是取代或未取代的萘基、蒽基、菲基、芘基、芴基、螺芴基、9,9-二甲基芴基、联萘基、联萘芴基等。In the embodiment of the present application, 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. In some embodiments, 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. Among them, 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. Among them, the polycyclic aromatic group can be a fused ring type or Non-fused ring type (such as biphenyls). Specifically, 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) . Wherein, for example, 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.
本申请实施方式中，上述涉及的取代或未取代的芳氧基可以是取代或未取代C6-C30芳氧基；芳氧基可以是单环芳氧基或多环芳氧基。一些实施例中，取代或未取代的芳氧基可以是取代或未取代的C6-C20芳氧基、取代或未取代的C6-C12芳氧基。具体可以是通过上述的芳基氧化得到的芳氧基。In the embodiment of the present application, 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. In some embodiments, 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. Specifically, it may be an aryloxy group obtained by the above-mentioned oxidation of an aryl group.
本申请实施方式中，上述涉及的取代或未取代的杂芳基可以是取代或未取代C3-C30杂芳基。一些实施例中，取代或未取代的杂芳基可以是取代或未取代的C5-C20杂芳基、取代或未取代的C6-C12杂芳基。杂芳基中的杂原子可以选自N、O、S、Se原子中的一种或多种。取代或未取代的杂芳基可以是取代或未取代的五元杂环、取代或未取代的六元杂环、取代或未取代的苯并杂环、取代或未取代的杂环并杂环等。示例性地，取代或未取代的杂芳基可以是吡啶基、苯基取代的吡啶基、喹啉基、呋喃基、苯并呋喃基、二苯并呋喃基、叔丁基取代的二苯并呋喃基、噻吩基、二苯并噻吩基、咔唑基、N-苯基咔唑基、氧杂蒽酮基、三嗪基、苯基取代的三嗪基等。In the embodiment of the present application, the above-mentioned substituted or unsubstituted heteroaryl group may be a substituted or unsubstituted C 3 -C 30 heteroaryl group. In some embodiments, 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. Exemplarily, the substituted or unsubstituted heteroaryl may be pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, benzofuryl, dibenzofuryl, tert-butyl-substituted dibenzoyl. Furyl, thienyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, xanthonyl, triazinyl, phenyl-substituted triazinyl, etc.
本申请实施方式中，上述涉及的取代或未取代的杂芳氧基可以是取代或未取代C3-C30杂芳氧基。一些实施例中，取代或未取代的杂芳氧基可以是取代或未取代的C5-C20杂芳氧基、取代或未取代的C6-C12杂芳氧基。杂芳氧基中的杂原子可以选自N、O、S、Se原子中的一种或多种。具体地，杂芳氧基可以是由上述的杂芳基氧化得到，此处不再赘述。In the embodiment of the present application, the above-mentioned substituted or unsubstituted heteroaryloxy group may be a substituted or unsubstituted C 3 -C 30 heteroaryloxy group. In some embodiments, 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.
本申请实施方式中，取代或未取代的烷基胺基为被取代或未取代的烷基所取代的氨基。取代或未取代的烷基胺基可以是取代或未取代C1-C30烷基胺基。一些实施例中，取代或未取代的烷基胺基可以是取代或未取代C2-C20烷基胺基、取代或未取代C3-C12烷基胺基。示例性地，取代或未取代的烷基胺基可以是乙基氨基等。In the embodiment of the present application, 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. In some embodiments, 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. Illustratively, the substituted or unsubstituted alkylamino group may be ethylamino and the like.
本申请实施方式中，取代或未取代的芳胺基为被取代或未取代的芳基所取代的氨基，具体可以是被上述取代或未取代的芳基所取代的氨基。取代或未取代的芳胺基可以是取代或未取代C6-C30芳胺基。一些实施例中，取代或未取代的芳胺基可以是取代或未取代C6-C20芳胺基、取代或未取代C7-C15芳胺基。示例性地，取代或未取代的芳胺基例如可以是苯基氨基、二甲基苯基氨基、叔丁基苯取代的氨基、二叔丁基苯基氨基等。In the embodiment of the present application, 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. In some embodiments, 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. Illustratively, the substituted or unsubstituted arylamine group may be, for example, phenylamino, dimethylphenylamino, tert-butylbenzene-substituted amino, di-tert-butylphenylamino, etc.
本申请实施方式中，上述取代或未取代的杂芳胺基为被取代或未取代的杂芳基所取代的氨基，具体可以是被上述取代或未取代的杂芳基所取代的氨基。取代或未取代的杂芳胺基可以是取代或未取代C3-C30杂芳胺基。一些实施例中，取代或未取代的杂芳胺基可以是取代或未取代的C5-C20杂芳胺基、取代或未取代的C6-C12杂芳胺基。In the embodiment of the present application, 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. In some embodiments, 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.
本申请实施方式中，上述取代或未取代的硼烷基可以是硼烷基、苯基取代的硼烷基等，取代的硼烷基中取代基可以是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基等。In the embodiment of the present application, 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. group, nitro, carboxyl, sulfonate, acyl, substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryl, substituted or unsubstituted Substituted aryloxy group, substituted or unsubstituted heteroaryl group, etc.
本申请实施方式中，取代或未取代的硅烷基可以是三甲基硅基等。本申请实施方式中， 取代或未取代的芳香硅基可以是苯基硅基等。In the embodiment of the present application, the substituted or unsubstituted silyl group may be trimethylsilyl group or the like. In the implementation of this application, The substituted or unsubstituted aromatic silicon group may be phenyl silicon group or the like.
本申请实施方式中，除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团可以是包括但不限于取代或未取代的酰亚胺基、取代或未取代的酰胺基、氰基、硝基或羟基。其中，取代的酰亚胺基、取代的酰胺基中的取代基可以但不限于是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基。In the embodiment of the present application, in addition to the above-mentioned groups, 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. Substituted imide group, substituted or unsubstituted amide group, cyano group, nitro group or hydroxyl group. Among them, 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.
本申请实施方式中，R1、R2每次出现独立地可以是氢原子、氘原子、氚原子、卤素原子、氰基、金刚烷基、甲基、氘代甲基、氚代甲基、氟代丙基、三氟甲基、乙基、氘代乙基、氚代乙基、异丙基、氘代异丙基、氚代异丙基、叔丁基、氘代叔丁基、氚代叔丁基、苯基取代的叔丁基、环戊基、氘代环戊基、氚代环戊基、甲基取代的环戊基、环己基、苯基、氘代苯基、氚代苯基、二联苯基、氘代二联苯基、氚代二联苯基、三联苯基、氘代三联苯基、氚代三联苯基、二苯醚基、甲基取代的二苯醚基、萘基、蒽基、菲基、芘基、吡啶基、苯基取代的吡啶基、喹啉基、呋喃基、噻吩基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基、叔丁基取代的二苯并呋喃基、咔唑基、N-苯基咔唑基、叔丁基取代的咔唑基、叔丁基取代的N-咔唑基苯基、9,9-二甲基芴基、螺芴基、甲基取代的苯基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、二联苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、苯基取代的氨基、叔丁基苯取代的氨基、叔丁基取代的二苯并呋喃基、苯基取代的叔丁基、氧杂蒽酮基、三嗪基、苯基取代的三嗪基、硼烷基、苯基取代的硼烷基、甲氧基或叔丁氧基。In the embodiment of the present application, 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, cyclohexyl, phenyl, deuterated phenyl, tritiated Phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether group, methyl substituted diphenyl ether base, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl , tert-butyl-substituted dibenzofuranyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted carbazolyl, tert-butyl-substituted N-carbazolylphenyl, 9,9- Dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, diphenyl, methyl-substituted di-phenyl Biphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl , deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted diphenyl, deuterated ethyl substituted diphenyl, deuterated isopropyl substituted Diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthonyl, triazinyl, phenyl-substituted triazinyl, boryl, phenyl-substituted boryl, methoxy or tert-butoxy.
本申请一些实施方式中，部分相邻的R1连接成环，其余R1可独立的选自上述的可选基团。其中，当相邻的R1连接成环(即邻近的Z连接成环)时，所形成的环结构包括但不限于是式(a)至式(i)所示的任意一种：
In some embodiments of the present application, some adjacent R 1s are connected to form a ring, and the remaining R 1s can be independently selected from the above optional groups. Wherein, when adjacent R 1 are connected to form a ring (that is, adjacent Z are connected to form a ring), the ring structure formed includes but is not limited to any one shown in formula (a) to formula (i):
式(a)至式(i)中，*标记的位置为连接位置，式(a)至式(i)的结构通过*标记的位置以并环方式进行连接。其中，对应式(a)的情况可参见下文式(7)所示的化合物；对应式(b)的情况可参见下文式(9)所示的化合物；对应式(c的情况可参见下文式(10)所示的化合物；对应式(d)的情况可参见下文式(19)所示的化合物；对应式(e)的情况可参见下文式(11)所示的化合物；对应式(f)的情况可参见下文式(15)所示的化合物；对应式(g)的情况可参见下文式(16)所示的化合物；对应式(h)的情况可参见下文式(18)所示的化合物；对应式(i)的情况可参见下文式(67)至式(78)所示的化合物。本申请一 些实施例中，式(a)至式(i)所示的结构中，可取代的位置上可以具有取代基，取代基例如可以是氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基等。上述式(a)至式(i)所示的不同结构有利于化合物发光光色的可控调节。In 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 *. Among them, for the case corresponding to formula (a), 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 compound represented by (10); for the case corresponding to formula (d), please refer to the compound represented by formula (19) below; for the case corresponding to formula (e), please refer to the compound represented by formula (11) below; corresponding to formula (f) ), please refer to the compound represented by formula (15) below; for the corresponding formula (g), please refer to the compound represented by formula (16) below; for the corresponding formula (h), please refer to the compound represented by formula (18) below Compounds; for the situation corresponding to formula (i), please refer to the compounds represented by formula (67) to formula (78) below. In this application In some embodiments, in the structures represented by formula (a) to formula (i), 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.
本申请一些实施方式中，R1与R2连接成环，参与成环的可以是一个或多个R1，其余未参与成环的R1可独立的选自上述的可选基团。其中，当R2与邻近的R1连接成环(即Y与邻近的Z连接成环)时，所形成的环结构可以是包括式(A)至式(D)所示的结构：
In some embodiments of the present application, 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. Wherein, when R 2 is connected to the adjacent R 1 to form a ring (that is, Y is connected to the adjacent Z to form a ring), the ring structure formed may include structures shown in formulas (A) to (D):
式(A)中R5为氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基，n为0至4的整数；式(A)至式(D)中，*标记的位置为连接位置，式(A)至式(D)的结构通过*标记的位置以并环方式进行连接。其中，对应式(A)的情况的化合物可以是如式(Ⅱ-A)所示的化合物，也可参见下文式(115)所示的化合物；In the formula (A), 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), the positions marked with * are connection positions, and the structures of formulas (A) to (D) are connected in a parallel ring manner through the positions marked with *. Among them, 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;
式(Ⅱ-A)，式(Ⅱ-A)中，Y的选择与上文一致。 Formula (II-A), in formula (II-A), the selection of Y is consistent with the above.
本申请实施方式中，式(I)至式(X)所示化合物具体可以是包括结构式如式(1)-(268)所示的化合物中的任意一种：















In the embodiment of the present application, 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):















本申请实施例提供的化合物可以采用各种化学上可实现的方式进行制备获得。The compounds provided in the examples of this application can be prepared in various chemically feasible ways.
本申请一些实施方式中，通式(I)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (I) can be synthesized according to the following steps:
(1)将原料1A加入反应容器中，再加入原料2A，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1A；(1) Add raw material 1A into the reaction vessel, then add raw material 2A, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1A;
(2)将中间体1A加入反应容器中，再加入原料3A,tBuONa,tBu3P,Pd2(dba)3和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体2A； (2) Add intermediate 1A into the reaction vessel, then add raw materials 3A, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 2A;
(3)将中间体2A加入反应容器中，依次加入原料4A,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体3A；(3) Add intermediate 2A into the reaction vessel, add raw materials 4A, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 3A;
(4)将中间体3A加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热搅拌，然后降低温度至0℃，加入iPr2-N-Et(二异丙基乙胺)，继续加热回流搅拌，随后直接旋干，通过硅胶柱层析分离得到通式(I)所示的化合物。反应过程如下所示：
(4) Add intermediate 3A into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and stir, then lower the temperature to 0°C, add iPr 2 -N-Et (diisopropyl ethyl amine), continue to heat and stir under reflux, then directly spin to dryness, and separate through silica gel column chromatography to obtain the compound represented by general formula (I). The reaction process is as follows:
本申请一些实施方式中，通式(II)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (II) can be synthesized according to the following steps:
(1)将原料1B加入反应容器中，再加入原料2B，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1；(1) Add raw material 1B into the reaction vessel, then add raw material 2B, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1;
(2)将中间体1B加入反应容器中，再加入原料3B,tBuONa,tBu3P,Pd2(dba)3和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体2B；(2) Add intermediate 1B into the reaction vessel, then add raw materials 3B, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 2B;
(3)将中间体2B加入反应容器中，依次加入原料4B,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体3B；(3) Add intermediate 2B into the reaction vessel, add raw materials 4B, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 3B;
(4)将中间体3B加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热搅拌，然后降低温度至0℃，加入iPr2-N-Et，继续在180℃下搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(II)所示的化合物。反应过程如下所示：

(4) Add intermediate 3B to the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and stir, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue at 180°C Stir and reflux for 3 hours, then directly spin to dryness, and separate through silica gel column chromatography to obtain the compound represented by general formula (II). The reaction process is as follows:

本申请一些实施方式中，通式(III)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (III) can be synthesized according to the following steps:
(1)将原料1C加入反应容器中，再加入原料2C，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1C；(1) Add raw material 1C into the reaction vessel, then add raw material 2C, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1C;
(2)将中间体1C加入反应容器中，再加入原料3C,tBuONa,tBu3P,Pd2(dba)3和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体2C；(2) Add intermediate 1C into the reaction vessel, then add raw materials 3C, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 2C;
(3)将中间体2C加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热回流搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(III)所示的化合物。反应过程如下所示：
(3) Add intermediate 2C into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and reflux and stir overnight, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue stirring and refluxing 3h, then directly spin to dryness, and separated by silica gel column chromatography to obtain the compound represented by general formula (III). The reaction process is as follows:
本申请一些实施方式中，通式(IV)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (IV) can be synthesized according to the following steps:
(1)将原料1D加入反应容器中，再加入原料2D，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1D；(1) Add raw material 1D into the reaction vessel, then add raw material 2D, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1D;
(2)将中间体1D加入反应容器中，再加入原料3D,K2CO3,Pd(PPh3)4(四(三苯基膦)钯)和DMF、H2O,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体2D； (2) Add intermediate 1D into the reaction vessel, then add raw materials 3D, K 2 CO 3 , Pd(PPh 3 ) 4 (tetrakis (triphenylphosphine) palladium), DMF and H 2 O, then replace nitrogen and heat Stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 2D;
(3)将中间体2D加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热回流搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(IV)所示的化合物。反应过程如下所示：
(3) Add intermediate 2D into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and reflux and stir overnight, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue stirring and refluxing 3h, then directly spin to dryness, and separated by silica gel column chromatography to obtain the compound represented by general formula (IV). The reaction process is as follows:
本申请一些实施方式中，通式(V)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (V) can be synthesized according to the following steps:
(1)将原料1E加入反应容器中，再加入原料2E，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1E；(1) Add raw material 1E into the reaction vessel, then add raw material 2E, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1E;
(2)将中间体1E加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热回流搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(V)所示的化合物。反应过程如下所示：
(2) Add intermediate 1E to the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and reflux and stir overnight, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue stirring and refluxing 3h, then directly rotated to dryness, and separated by silica gel column chromatography to obtain the compound represented by general formula (V). The reaction process is as follows:
本申请一些实施方式中，通式(VI)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (VI) can be synthesized according to the following steps:
(1)将原料1F加入反应容器中，再加入原料2F，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1F； (1) Add raw material 1F into the reaction vessel, then add raw material 2F, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1F;
(2)将中间体1F加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热回流搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(VI)所示的化合物。反应过程如下所示：
(2) Add intermediate 1F into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and reflux and stir overnight, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue stirring and refluxing 3h, then directly spin to dryness, and separated by silica gel column chromatography to obtain the compound represented by general formula (VI). The reaction process is as follows:
本申请一些实施方式中，通式(VII)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (VII) can be synthesized according to the following steps:
(1)将原料1G加入反应容器中，再加入原料2G，K2CO3，CuI，L-Proline(L-脯氨酸)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1G；(1) Add raw material 1G into the reaction vessel, then add raw material 2G, K 2 CO 3 , CuI, L-Proline (L-proline) and p-xylene, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1G;
(2)将中间体1G加入到反应容器中，加入邻二氯苯，氮气保护，冰水浴降温后加入nBu-Li,室温搅拌反应充分后，冰水浴降温，加入BBr3，室温搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(VII)所示的化合物。反应过程如下所示：
(2) Add intermediate 1G into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, add nBu-Li after cooling in an ice-water bath, stir at room temperature. After the reaction is complete, cool down in an ice-water bath, add BBr 3 , stir at room temperature overnight, and then Lower the temperature to 0°C, add iPr 2 -N-Et, continue to stir and reflux for 3 hours, then directly spin to dryness, and separate through silica gel column chromatography to obtain the compound represented by general formula (VII). The reaction process is as follows:
本申请一些实施方式中，通式(VIII)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (VIII) can be synthesized according to the following steps:
(1)将原料1H加入反应容器中，再加入原料2H，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1H；(1) Add raw material 1H into the reaction vessel, then add raw material 2H, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1H;
(2)将中间体1H加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热回流搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(VIII)所示的化合物。反应过程如下所示：
(2) Add intermediate 1H into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and reflux and stir overnight, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue stirring and refluxing 3h, then directly spin to dryness, and separated by silica gel column chromatography to obtain the compound represented by general formula (VIII). The reaction process is as follows:
本申请一些实施方式中，通式(IX)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (IX) can be synthesized according to the following steps:
(1)将原料1I加入反应容器中，再加入原料2，K2CO3，CuI，L-Proline(L-脯氨酸)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1I；(1) Add raw material 1I into the reaction vessel, then add raw material 2, K 2 CO 3 , CuI, L-Proline (L-proline) and p-xylene, then replace nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1I;
(2)将中间体1I加入到反应容器中，加入邻二氯苯，氮气保护，冰水浴降温后加入nBu-Li,室温搅拌反应充分后，冰水浴降温，加入BBr3，室温搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(IX)所示的化合物。反应过程如下所示：
(2) Add intermediate 1I to the reaction vessel, add o-dichlorobenzene, protect with nitrogen, add nBu-Li after cooling in an ice-water bath, stir at room temperature. After the reaction is sufficient, cool down in an ice-water bath, add BBr 3 , stir at room temperature overnight, and then Lower the temperature to 0°C, add iPr 2 -N-Et, continue to stir and reflux for 3 hours, then directly spin to dryness, and separate through silica gel column chromatography to obtain the compound represented by general formula (IX). The reaction process is as follows:
本申请一些实施方式中，通式(X)所示的化合物可以是按照如下步骤进行合成：In some embodiments of the present application, the compound represented by general formula (X) can be synthesized according to the following steps:
(1)将原料1J加入反应容器中，再加入原料2J，tBuONa(叔丁醇钠)，tBu3P(三叔丁基膦)，Pd2(dba)3(三(二亚苄基丙酮)二钯)和对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1J；(1) Add raw material 1J into the reaction vessel, then add raw material 2J, tBuONa (sodium tert-butoxide), tBu 3 P (tri-tert-butyl phosphine), Pd 2 (dba) 3 (tris (dibenzylidene acetone) Dipalladium) and p-xylene, then replaced with nitrogen, heated and stirred. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1J;
(2)将中间体1J加入到反应容器中，加入邻二氯苯，氮气保护，随后加入BBr3，加热回流搅拌过夜，然后降低温度至0℃，加入iPr2-N-Et，继续搅拌回流3h，随后直接旋干，通过硅胶柱层析分离得到通式(X)所示的化合物。反应过程如下所示：
(2) Add intermediate 1J into the reaction vessel, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and reflux and stir overnight, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue stirring and refluxing 3h, and then directly spin to dryness, and then separated by silica gel column chromatography to obtain the compound represented by the general formula (X). The reaction process is as follows:
本申请实施例提供的上述化合物具有较高的荧光量子效率、较窄的半峰宽，可用于各种具有发光、显示、照明等功能的电子器件中，提升器件性能。本申请实施例提供上述的化合物及其盐在电致发光器件、有机发光场效应晶体管、有机光伏器件、发光电化学电池、光电 转换器、开光器件、图像传感器、激光器或感光器件中的应用。具体地，上述化合物在上述器件中可以用作发光材料。例如，本申请实施例提供的上述化合物能够应用于有机电致发光器件中，可作为有机电致发光器件发光层的材料，能够提升器件的发光效率、发光稳定性、色纯度、寿命等。具体地，本申请实施例化合物具有窄半峰宽、高荧光量子产率，以及具有合适的HOMO和LUMO能级，可用作有机电致发光器件的发光层掺杂材料，从而提升器件效率、发光色纯度和器件稳定性；将本申请实施例化合物作为掺杂材料引入到发光层中，能够起到激子敏化作用，有效提升器件效率和寿命。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. Specifically, the above-mentioned compounds can be used as light-emitting materials in the above-mentioned devices. For example, 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. Specifically, 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.
本申请实施例提供一种电子器件，电子器件包括本申请实施例上述的化合物。电子器件例如可以是有机电致发光器件、有机发光场效应晶体管、有机光伏器件、发光电化学电池等。参见图1，图1为本申请一实施例提供的有机电致发光器件(OLEDs)100的结构示意图。图1所示的有机电致发光器件100包括阳极10、阴极20以及位于阳极10和阴极20之间的功能层30，功能层30包括发光层301。发光层301包含本申请实施例提供的上述化合物。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. Referring to Figure 1, 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.
本申请一些实施方式中，发光层301含有主体材料和掺杂材料(也可称为“客体材料”)，其中，掺杂材料包括至少一种本申请上述的化合物。所述化合物作为发光层301的掺杂材料，其能起到敏化激子的作用，提升器件的发光效率；所述化合物半峰宽较窄，能够提升器件的发光色纯度，提高器件的色域，使器件能够符合更高要求的显示标准；所述化合物具有合适的HOMO能级和LUMO能级，能有效降低主体材料的三线态激子浓度，降低三线态激子的淬灭几率，可有效提升器件的稳定性和寿命。In some embodiments 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. As a doping material of the light-emitting layer 301, 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. domain, enabling the device to meet higher requirements for display standards; 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.
本申请实施方式中，发光层301的掺杂材料可以是仅包括一种或多种本申请上述的化合物；也可以是同时包括一种或多种本申请上述的化合物和其他掺杂材料。其中其他掺杂材料可以是各种本领域可用的掺杂材料，具体可以根据实际需要选择。In the embodiment of the present application, 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.
本申请实施方式中，发光层301的主体材料可以是包括一种或多种，主体材料可以是各种本领域可用的主体材料，具体可以根据实际需要选择。In the embodiment of the present application, 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.
本申请一些实施方式中，发光层301中包括两种主体材料，这两种主体材料可分别称为第一主体材料、第二主体材料，该第一主体材料和第二主体材料中的至少一个为热活化延迟荧光(TADF)材料。该实施方式中，发光层的主体材料通过两种材料搭配而成，其与作为掺杂材料的上述的化合物之间的能量传递效率较高，可以使化合物的发光潜能得到充分发挥，器件的发光效率更高。In some embodiments of the present application, 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. In this embodiment, 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.
本申请实施方式中，阳极10和阴极20的构成材料为导电材料，可以独立地选自导电金属、导电金属氧化物、导电聚合物等。其中，导电金属可以包括镁(Mg)、铝(Al)、金(Au)、银(Ag)、铂(Pt)、靶(Pd)等金属单质及其合金中的一种或多种；导电金属氧化物包括但不限于氧化铟锡(ITO)、氧化铟锌(IZO)、掺铝氧化锌(AZO)、掺氟二氧化锡(FTO)、掺磷二氧化锡(PTO)等中的一种或多种；导电聚合物包括但不限于聚噻吩、聚吡咯、聚苯胺等。In the embodiment of the present application, 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. Among them, 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. One or more kinds; conductive polymers include but are not limited to polythiophene, polypyrrole, polyaniline, etc.
本申请实施方式中，参见图1，功能层30还包括位于阳极10和发光层301之间的第一载流子传输层302，以及位于阴极20和发光层301之间的第二载流子传输层303。其中，第一载流子传输层302可以是包括位于阳极10与发光层301之间的空穴注入层3021、空穴传输层3022、电子阻挡层3023中的一种或多种。其中，空穴注入层3021位于阳极10与空穴传输层3022之间，电子阻挡层3023位于发光层301与空穴传输层3022之间。第二载流子传输层303可以是包括位于阴极20与发光层301之间的电子注入层3031、电子传输层3032、空穴阻挡层3033中的一种或多种。其中，电子注入层3031位于阴极20与电子传输层3032 之间，空穴阻挡层3033位于阴极20与空穴传输层3022之间。一些实施例中，如图1所示，有机电致发光器件100包括依次设置的阳极10、空穴注入层3021、空穴传输层3022、电子阻挡层3023、发光层301、空穴阻挡层3033、电子传输层3032、电子注入层3031。需要说明的是功能层30的各层并非全部必需，但发光层301是必需的。例如，功能层30沿阳极10向阴极20的方向，也可以依次包括“发光层301/电子传输层3032”的层叠结构，或者包括“发光层301/电子注入层3031”的层叠结构，或者包括“空穴注入层3021/发光层301/电子传输层3032”的层叠结构，或者包括“空穴注入层3021/发光层301/电子注入层3031”的层叠结构，或者包括“空穴传输层3022/发光层301/电子传输层3032”的层叠结构，或者包括“空穴注入层3021/空穴传输层3022/发光层301/电子传输层3032”的层叠结构，或者包括“空穴注入层3021/空穴传输层3022或电子阻挡层3023/发光层301/空穴阻挡层3033或电子传输层3032/电子注入层3031”的层叠结构，或者包括“空穴注入层3021/空穴传输层3022/电子阻挡层3023/发光层301/空穴阻挡层3033或电子传输层3032/电子注入层3031”的层叠结构等。其中“/”表示各层分界。本申请中，对以上各层的厚度没有特定的限制，本领域技术人员可根据实际需要确定。上述各层的材料为本领域的常规选择，本申请无特殊限定。In the embodiment of the present application, referring to FIG. 1 , 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 . Transport layer 303. 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. Among them, the hole injection layer 3021 is located between the anode 10 and the hole transport layer 3022, and 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. Among them, the electron injection layer 3031 is located on the cathode 20 and the electron transport layer 3032 Between them, the hole blocking layer 3033 is located between the cathode 20 and the hole transport layer 3022. In some embodiments, as shown in FIG. 1 , 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. , electron transport layer 3032, electron injection layer 3031. It should be noted that not all of the layers of the functional layer 30 are necessary, but the light-emitting layer 301 is necessary. For example, 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 or electron blocking layer 3023/Light-emitting layer 301/Hole blocking layer 3033 or electron transport layer 3032/Electron injection layer 3031" stacked structure, or including "hole injection layer 3021/hole transport layer 3022 A stacked structure of /electron blocking layer 3023/light emitting layer 301/hole blocking layer 3033 or electron transport layer 3032/electron injection layer 3031", etc. Among them, "/" represents the boundary between each layer. In this application, there is no specific limit to the thickness of each of the above layers, and those skilled in the art can determine it according to actual needs. The materials of each of the above layers are conventional choices in this field and are not specifically limited in this application.
在一些实施方式中，有机电致发光器件100还可以具有基板40(如图1所示)。基板40可以是位于阳极10远离功能层30的一侧(如图1所示)，此时，有机电致发光器件100为底发射器件。基板40也可以是位于阴极20远离功能层30的一侧，此时有机电致发光器件100为顶发射器件，顶发射器件包括依次设置在基板40上的阴极20、功能层30和阳极10。基板40可以作为整个有机电致发光器件100的支撑部，其材质可以为石英、玻璃、单质硅、金属、塑料等。在一些实施方式中，基板40为对光透明的玻璃或塑料。基板40的形状可根据具体应用场景而定，例如可以形成为板状、膜状或片状等。基板40的厚度没有特别限定。In some embodiments, 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 ). In this case, 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. In this case, 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.
本申请中，对阳极10、阴极20及功能层30各层的制备工艺没有特别限制，可以采用物理气相沉积法、化学气相沉积法或涂布法等方式制备。其中，物理气相沉积法可以包括真空蒸镀法(如电阻蒸发源蒸镀法、电子束蒸发源蒸镀法、脉冲激光沉积法等)、溅镀法(如磁控溅射法)等中的一种或多种；涂布法可以包括溶液旋涂、浸涂、刮涂、喷涂、辊涂、喷墨印刷、丝网印刷法等方式。一般地，阳极10和阴极20可通过真空蒸镀法制备，功能层30的各层可通过真空蒸镀法或涂布法制备。以图1所示的有机电致发光器件的制备为例，可先在基板40上形成阳极10，再在阳极10上依次形成包含发光层301的功能层30，随后在功能层30上形成阴极20。在本申请其他实施方式中，可以在基板40上依序形成阴极20，包含发光层301的功能层30，随后在功能层30上形成阳极10。In this application, there are no special restrictions on the preparation process of each layer of the anode 10, the cathode 20 and the functional layer 30, and they can be prepared by physical vapor deposition, chemical vapor deposition or coating. Among them, 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. Generally, 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. Taking the preparation of the organic electroluminescent device shown in FIG. 1 as an example, 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. In other embodiments of the present application, 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 .
参见图2，本申请实施例还提供了一种显示装置200，显示装置200包括本申请实施例上述的电子器件，具体可以是包括上述的有机电致发光器件100。Referring to FIG. 2 , 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 .
本申请实施方式中，显示装置200可以是手机、平板电脑、笔记本电脑、可穿戴设备(如智能手表、智能手环等)、电视机、数码相机、摄录机、播放机、微显示设备(如智能眼镜、虚拟现实(Virtual Reality，VR)设备、增强现实(Augmented Reality，AR)设备、电话机、打印机、交通工具、家用电器、广告牌、信息板、汽车中控屏等任何具有显示功能的产品或者部件中的视觉显示装置。In the embodiment of the present application, 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. A visual display device in a product or component.
本申请实施例还提供了一种照明装置，包括本申请实施例上述的电子器件，具体可以是包括上述的有机电致发光器件100。照明装置可以列举使用有机电致发光器件的汽车尾灯、汽车前照灯、汽车雾灯、室内照明装置(包括商用或家用等，例如台灯、天花板灯等)、室外照明装置(如路灯)、液晶显示装置的背光源等。 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.
参见图3，本申请实施例还提供一种电子设备300，电子设备300包括本申请实施例上述的显示装置200。电子设备300可以是手机、平板电脑、笔记本电脑、可穿戴设备(如智能手表、智能手环等)、电视机、数码相机、摄录机、播放机、微显示设备(如智能眼镜、虚拟现实(Virtual Reality，VR)设备、增强现实(Augmented Reality，AR)设备、电话机、打印机、交通工具、家用电器、广告牌、信息板、汽车中控屏等任何具有显示功能的电子产品。Referring to FIG. 3 , 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.
下面分多个实施例对本申请实施例进行进一步的说明。The embodiments of the present application will be further described below in multiple embodiments.
实施例1Example 1
具有式(4)结构式的化合物(以下简称为化合物4)的合成：Synthesis of compounds with the structural formula (4) (hereinafter referred to as compound 4):
(1)将原料1a加入烧瓶中，依次加入原料2a,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1a。(1) Add raw material 1a into the flask, add raw material 2a, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace with nitrogen, heat and stir. After the reaction is completed, the reaction solution is concentrated and separated by column chromatography to obtain intermediate 1a.
(2)将中间体1a加烧瓶中，依次加入原料3a,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体2a。(2) Add intermediate 1a to the flask, add raw materials 3a, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 2a.
(3)将中间体2a加烧瓶中，依次加入原料4a,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体3a。(3) Add intermediate 2a to the flask, add raw materials 4a, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 3a.
(4)将中间体3a加入到瓶中，加入邻二氯苯，氮气保护，随后加入BBr3，加热搅拌，然后降低温度至0℃，加入iPr2-N-Et，继续加热搅拌至反应结束，随后直接旋干，通过硅胶柱层析分离得到化合物4。(4) Add intermediate 3a to the bottle, add o-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and stir, then lower the temperature to 0°C, add iPr 2 -N-Et, continue to heat and stir until the reaction is completed. , then directly spin to dryness, and then separated by silica gel column chromatography to obtain compound 4.
上述合成工艺的反应过程如下所示：
The reaction process of the above synthesis process is as follows:
图4为本申请实施例1制备的化合物4的LC-MS(液相色谱-质谱联用)图谱。MS：测定值：849.45[M+H]+，理论值：848.45。图5和图6分别为本申请实施例1制备的化合物4的核磁共振氢谱和核磁共振碳谱。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.
实施例2Example 2
具有式(32)结构式的化合物(以下简称为化合物32)的合成：Synthesis of compounds with the structural formula (32) (hereinafter referred to as compound 32):
(1)将原料1b加入烧瓶中，依次加入原料2A,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1b。 (1) Add raw material 1b into the flask, then add raw materials 2A, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace with nitrogen, heat and stir. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 1b.
(2)将中间体1b加烧瓶中，依次加入原料3B,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体2b。(2) Add intermediate 1b to the flask, add raw materials 3B, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 2b.
(3)将中间体2b加烧瓶中，依次加入原料4a-1,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体3b。(3) Add intermediate 2b to the flask, add raw materials 4a-1, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 3b.
(4)将中间体3b加入到瓶中，加入间二氯苯，氮气保护，随后加入BBr3，加热搅拌，然后降低温度至0℃，加入iPr2-N-Et，继续加热搅拌直至反应结束，随后直接旋干，通过硅胶柱层析分离得到化合物32。该实施例制备的化合物32的核磁氢谱数据如图8所示。(4) Add intermediate 3b to the bottle, add m-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and stir, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue to heat and stir until the reaction is completed. , then directly spin to dryness, and then separated by silica gel column chromatography to obtain compound 32. The hydrogen nuclear magnetic spectrum data of compound 32 prepared in this example are shown in Figure 8.
上述合成工艺的反应过程如下所示：
The reaction process of the above synthesis process is as follows:
实施例3Example 3
具有式(139)结构式的化合物(以下简称为化合物139)的合成：Synthesis of a compound with the structural formula (139) (hereinafter referred to as compound 139):
(1)将原料1c加入烧瓶中，依次加入原料2c,tBuONa,tBu3P,Pd2(dba)3，对二甲苯,随后置换氮气，加热搅拌。反应结束后浓缩反应液并通过柱层析分离得到中间体1c。(1) Add raw material 1c into the flask, then add raw material 2c, tBuONa, tBu 3 P, Pd 2 (dba) 3 and p-xylene in sequence, then replace nitrogen, heat and stir. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 1c.
(2)将中间体1c加烧瓶中，用THF溶解，冰水浴下加入原料B(OMe)3并在常温下反应1h,然后降温至-78℃，滴加nBu-Li并反应2h,随后采用乙酸中和体系中的碱，再升温至0℃，滴加H2O2，通过硅胶柱层析分离得到中间体2c。(2) Add intermediate 1c to the flask, dissolve it in THF, add raw material B (OMe) 3 in an ice water bath and react at room temperature for 1 hour, then cool to -78°C, add nBu-Li dropwise and react for 2 hours, and then use Acetic acid neutralizes the alkali in the system, and then the temperature is raised to 0°C, H 2 O 2 is added dropwise, and intermediate 2c is obtained by silica gel column chromatography.
(3)将中间体2c加烧瓶中，依次加入原料3c,K2CO3，随后置换氮气，加入干燥的DMF溶剂，在常温下搅拌反应直至反应结束。反应结束后浓缩反应液并通过柱层析分离得到中间体3c。(3) Add intermediate 2c to the flask, add raw material 3c and K 2 CO 3 in sequence, then replace nitrogen, add dry DMF solvent, and stir the reaction at room temperature until the reaction is completed. After the reaction, the reaction solution was concentrated and separated by column chromatography to obtain intermediate 3c.
(4)将中间体3c加入到瓶中，加入间二氯苯，氮气保护，随后加入BBr3，加热搅拌，然后降低温度至0℃，加入iPr2-N-Et，继续加热搅拌直至反应结束，随后直接旋干，通过硅胶柱层析分离得到化合物139。该实施例制备的化合物139的核磁氢谱数据如图10所示。(4) Add intermediate 3c to the bottle, add m-dichlorobenzene, protect with nitrogen, then add BBr 3 , heat and stir, then lower the temperature to 0°C, add iPr 2 -N-Et, and continue to heat and stir until the reaction is completed. , then directly spin to dryness, and then separated by silica gel column chromatography to obtain compound 139. The hydrogen nuclear magnetic spectrum data of compound 139 prepared in this example is shown in Figure 10.
上述合成工艺的反应过程如下所示：
The reaction process of the above synthesis process is as follows:
将实施例1制备的化合物4、32和139进行紫外吸收光谱测试、荧光光谱测试，检测结果如表1和图7、图9、图11所示。其中，图7为本申请实施例1中化合物4的紫外吸收光谱和荧光光谱图。其中，吸收峰通过双光束紫外可见分光光度计进行测试；发光峰和FWHM(半峰宽)在薄膜状态下由荧光光谱仪测试得到；斯托克斯位移(Stokes shift)是指荧光光谱较相应的吸收光谱的红移，通过发射峰峰值减去吸收峰峰值计算得到。对比例的发光峰和FWHM通过采购商业化Ir(ppy)3测试薄膜得到。Compounds 4, 32 and 139 prepared in Example 1 were subjected to ultraviolet absorption spectrum testing and fluorescence spectrum testing. The detection results are shown in Table 1 and Figures 7, 9 and 11. Among them, Figure 7 is the ultraviolet absorption spectrum and fluorescence spectrum of compound 4 in Example 1 of the present application. Among them, 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.
表1
Table 1
由表1数据可知，化合物4、化合物32、化合物139具有小的斯托克斯位移(仅为22nm)，说明该材料能够被发射可见光的敏化材料很好的敏化。除此之外，化合物4、化合物32、化合物139具备很窄的半峰宽(FWHM＝27nm)，作为掺杂材料掺杂于主体材料中制备OLED器件，能够实现窄峰宽发射，从而实现高色纯度。It can be seen from the data in Table 1 that 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. In addition, compound 4, compound 32, and compound 139 have a very narrow half-peak width (FWHM=27nm). As doping materials, they are doped into the host material to prepare OLED devices, which can achieve narrow peak width emission, thereby achieving high Color purity.
采用商业化磷光材料Ir(ppy)3(全名为fac-Tris(2-phenylpyridine)iridium(III))作为对比例，可以看出，本申请实施例的化合物的斯托克斯位移远远小于商业化磷光材料Ir(ppy)3，说明本申请提供的化合物不仅可以通过普通的掺杂体系制备器件，还可以利用敏化的方式制备器件，而对比例则没有这样的优势，除此之外，化合物光谱FWHM远远窄于对比例的Ir(ppy)3材料，能够有效提升器件色域，提升器件的发光效率。Using 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. However, the comparative example does not have such advantages. In addition, , 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.
以下通过器件实施例1和2以及器件比较例1详细说明本申请上述合成的化合物在有机电致发光器件中的应用效果。The application effects of the compounds synthesized above in the present application in organic electroluminescent devices will be described in detail below through Device Examples 1 and 2 and Device Comparative Example 1.
器件实施例1 Device Example 1
一种有机电致发光器件，如图12所示，该器件包括基板40(具体为透明玻璃基板)，以及依次层叠设置在基板40上的ITO阳极10(厚度为150nm)、第一空穴传输层3022a(TAPC材料，厚度为30nm)、第二空穴传输层3022b(TCTA材料，厚度为10nm)、电子阻挡层3023(mCP材料，厚度是10nm)、发光层301(PPF作为主体材料，DACT-II作为热延迟荧光敏化剂材料，化合物4作为荧光掺杂材料，主体材料、敏化剂材料、化合物4质量比为68:30:2，发光层膜厚为20nm)、空穴阻挡层3033(PPF材料，厚度为5nm)、电子传输层3032(BPhen材料，厚度是40nm)、电子注入层3031(LiF层，厚度为1nm)和阴极20(Al，厚度为100nm)。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 (PPF 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), and 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) and cathode 20 (Al, thickness is 100nm).
相关材料的结构式如下所示。
The structural formulas of related materials are shown below.
上述OLED发光器件的制备过程如下：对ITO阳极10进行洗涤，即依次进行清洗剂洗涤、纯水洗涤、干燥，再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极10上，利用真空蒸镀装置，蒸镀膜厚为30nm的TAPC作为第一空穴传输层3022a。接着蒸镀10nm厚度的TCTA作为第二空穴传输层3022b。随后蒸镀10nm厚度的mCP作为电子阻挡层3023。上述电子阻挡材料蒸镀结束后，制作OLED发光器件的发光层301，使用PPF主体材料，DACT-II作为热延迟荧光敏化剂材料，化合物4作为荧光掺杂材料，主体材料、敏化剂材料、化合物4按照质量比为68:30:2混掺，发光层301膜厚为20nm。在上述发光层301上，继续真空蒸镀PPF，膜厚为5nm，此层为空穴阻挡层3033。在上述空穴阻挡层3033上，继续真空蒸镀40nm厚的BPhen作为电子传输层3032和1nm LiF作为电子注入层3031，在电子注入层3031上，通过真空蒸镀装置，制作膜厚为100nm的Al电极层，此层为阴极20。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. On the ITO anode 10 after the above cleaning, a vacuum evaporation device was used to evaporate TAPC with a film thickness of 30 nm as the first hole transport layer 3022a. Then, TCTA with a thickness of 10 nm is evaporated as the second hole transport layer 3022b. Then mCP with a thickness of 10 nm was evaporated as the electron blocking layer 3023. After the evaporation of the above-mentioned electron blocking material is completed, 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. On 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. On the above-mentioned hole blocking layer 3033, continue to vacuum evaporate 40nm thick BPhen as the electron transport layer 3032 and 1nm LiF as the electron injection layer 3031. On the electron injection layer 3031, use a vacuum evaporation device to produce a film thickness of 100nm. Al electrode layer, this layer is the cathode 20.
器件实施例2Device Example 2
器件实施例2与器件实施例1区别仅在于发光层301不同。在该实施例中，发光层301使用PPF主体材料，DACT-II作为热延迟荧光敏化剂材料，化合物4作为荧光掺杂材料，主体材料、敏化剂材料、化合物4质量比为78:20:2。The only difference between Device Embodiment 2 and Device Embodiment 1 is that the light-emitting layer 301 is different. In this embodiment, 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.
器件比较例1与器件实施例1的区别仅在于，发光层301采用CBP与Ir(ppy)3按质量比97:3混掺。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.
如上所述地完成OLED发光器件制备后，用公知的驱动电路将阳极和阴极连接起来，测量器件的起亮电压、外量子效率和半高带宽。所得器件的起亮电压、外量子效率和半高带宽的测试结果如表2和图13、图14和图15所示。其中，图13为本申请器件实施例1和器件实施例2的器件的发光光谱图；图14为本申请器件实施例1和器件实施例2的器件的电流密度-电压-亮度图；图15为本申请器件实施例1和器件实施例2的器件的亮度-外量子效率图。 由图14可获知器件的起亮电压，由图15可以获知器件的外量子效率。After the OLED light-emitting device is prepared as described above, a known driving circuit is used to connect the anode and the cathode, and the lighting voltage, external quantum efficiency and half-maximum bandwidth of the device are measured. The test results of the lighting voltage, external quantum efficiency and half-high bandwidth of the obtained device are shown in Table 2 and Figure 13, Figure 14 and Figure 15. Among them, Figure 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.
表2
Table 2
注：表2中器件的起亮电压、外量子效率、发光峰值使用IVL(电流-电压-亮度)测试系统测试；起亮电压在1cd/m2亮度下测试，外量子效率、发光峰值均在1000cd/m2下测试。Note: 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 .
由表2的器件数据结果可以看出，相对于器件比较例1的已知材料制备的器件，采用本申请实施例化合物制备的OLED器件，外量子效率获得提升，器件发光峰的半高带宽大幅下降，提升了器件色纯度。本申请实施例提供的化合物作为掺杂材料具有较高窄的光谱FWHM，能够有效提升器件色域，提升器件的发光效率，还能够提高发光稳定性。此外，采用本申请实施例化合物制备的OLED器件起亮电压较低。 It can be seen from the device data results in Table 2 that compared with the device made of known materials in Device Comparative Example 1, 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. As a doping material, 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. In addition, the OLED device prepared using the compounds of the embodiments of the present application has a lower lighting voltage.

Claims (19)

  1. 一种化合物，其特征在于，所述化合物为式(一)所示结构的多聚体：
    A compound, characterized in that the compound is a polymer with a structure represented by formula (1):
    其中，M2、M3分别为取代或未取代的芳环、取代或未取代的杂芳环、或取代或未取代的脂肪环；Z为C(R1)，Y为NR2、O、S或Se；R1、R2每次出现独立地选自氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的杂环烯基、取代或未取代的炔基、取代或未取代的环炔基、取代或未取代的杂环炔基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的烷基胺基、取代或未取代的芳胺基、取代或未取代的杂芳胺基、取代或未取代的硼烷基、取代或未取代的硅烷基、取代或未取代的芳香硅基、或除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团，相邻的R1可连接成环。Among them, 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 cycloalkynyl, substituted or unsubstituted heterocycloalkynyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted hetero Aryloxy group, substituted or unsubstituted alkylamino group, substituted or unsubstituted arylamine group, substituted or unsubstituted heteroarylamino group, substituted or unsubstituted borane group, substituted or unsubstituted silyl group, Substituted or unsubstituted aromatic silicon group, or C 1 -C 18 electron-withdrawing group containing at least one heteroatom among O, N, S, B, P, F other than the above groups, adjacent R 1 can be connected to form a ring.
  2. 如权利要求1所述的化合物，其特征在于，所述化合物为2-6个所述式(一)所示结构的多聚体。The compound according to claim 1, characterized in that the compound is a polymer of 2-6 structures represented by the formula (1).
  3. 如权利要求1或2所述的化合物，其特征在于，所述化合物具有式(I)至式(X)所示的任意一种结构通式：

    The compound according to claim 1 or 2, characterized in that the compound has any one of the general structural formulas represented by formula (I) to formula (X):

    式(I)至式(X)中，Z为C(R1)，Y为NR2、O、S或Se；R1、R2每次出现独立地选自氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环烷基、取代或未取代的烯基、取代或未取代的环烯基、取代或未取代的杂环烯基、取代或未取代的炔基、取代或未取代的环炔基、取代或未取代的杂环炔基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的杂芳氧基、取代或未取代的烷基胺基、取代或未取代的芳胺基、取代或未取代的杂芳胺基、取代或未取代的硼烷基、取代或未取代的硅烷基、取代或未取代的芳香硅基、或除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团，相邻的R1可连接成环，R2可与邻近的R1连接成环。In 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 arylamine group, substituted Or unsubstituted heteroarylamino group, substituted or unsubstituted borane group, substituted or unsubstituted silyl group, substituted or unsubstituted aromatic silicon group, or other than the above groups containing O, N, S, B , the C 1 -C 18 electron-withdrawing group of at least one heteroatom in P or F, adjacent R 1 can be connected to form a ring, and R 2 can be connected to adjacent R 1 to form a ring.
  4. 如权利要求1-3任一项所述的化合物，其特征在于，所述取代的烷基、取代的环烷基、取代的杂环烷基、取代的烯基、取代的环烯基、取代的杂环烯基、取代的炔基、取代的环炔基、取代的杂环炔基、取代的烷氧基、取代的芳氧基、取代的芳基、取代的杂芳基、取代的杂芳氧基、取代的烷基胺基、取代的芳胺基、取代的杂芳胺基、取代的硼烷基、取代的硅烷基、取代的芳香硅基中的取代基包括氘原子、氚原子、卤素原子、氰基、硝基、羧基、磺酸基、酰基、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的芳氧基、取代或未取代的杂芳基中的一种或多种。The compound according to any one of claims 1 to 3, wherein the substituted alkyl, substituted cycloalkyl, substituted heterocycloalkyl, substituted alkenyl, substituted cycloalkenyl, substituted Heterocyclealkenyl, substituted alkynyl, substituted cycloalkynyl, substituted heterocycloalkynyl, substituted alkoxy, substituted aryloxy, substituted aryl, substituted heteroaryl, substituted hetero Substituents in aryloxy groups, substituted alkylamino groups, substituted arylamine groups, substituted heteroarylamino groups, substituted borane groups, substituted silyl groups, and substituted aromatic silicon groups include deuterium atoms and tritium atoms. , 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 aromatic group group, one or more of substituted or unsubstituted aryloxy groups, substituted or unsubstituted heteroaryl groups.
  5. 如权利要求1-4任一项所述的化合物，其特征在于，所述取代或未取代的烷基为取代或未取代C1-C30烷基；所述取代或未取代的环烷基为取代或未取代C3-C30环烷基；所述取代或未取代的杂环烷基为取代或未取代C2-C30杂环烷基；所述取代或未取代的烯基为取代或未取代C2-C30烯基；所述取代或未取代的环烯基为取代或未取代C3-C10环烯基；所述取代或未取代的杂环烯基为取代或未取代C2-C10杂环烯基；所述取代或未取代的炔基为取代或未取代C2-C30炔基；所述取代或未取代的环炔基为取代或未取代C6-C10环炔基；所述取代或未取代的杂环炔基为取代或未取代C5-C10杂环炔基；所述取代或未取代的烷氧基为取代或未取代C1-C30烷氧基；所述取代或未取代的芳氧基为取代或未取代C6-C30芳氧基；所述取代或未取代的芳基为取代或未取代C6-C30芳基；所述取代或未取代的杂芳基为取代或未取代C3-C30杂芳基；所述取代或未取代的杂芳氧基为取代或未取代C3-C30杂芳氧基；所述取代或未取代的烷基胺基为取代或未取代C1-C30烷基胺基；所述取代或未取代的芳胺基为取代或未取代C6-C30芳胺基；所述取代或未取代的杂芳胺基为取代或未取代C3-C30杂芳胺基。 The compound according to any one of claims 1 to 4, wherein 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 Substituted or unsubstituted C 2 -C 30 alkenyl; 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 -C 10 cycloalkynyl; the substituted or unsubstituted heterocyclic alkynyl is a substituted or unsubstituted C 5 -C 10 heterocyclic alkynyl; the substituted or unsubstituted alkoxy group is a substituted or unsubstituted C 1 -C 30 alkoxy group; the substituted or unsubstituted aryloxy group is a substituted or unsubstituted C 6 -C 30 aryloxy group; the substituted or unsubstituted aryl group is a substituted or unsubstituted C 6 -C 30 aryl; the substituted or unsubstituted heteroaryl is a substituted or unsubstituted C 3 -C 30 heteroaryl; the substituted or unsubstituted heteroaryloxy group is a substituted or unsubstituted C 3 -C 30 hetero Aryloxy group; the substituted or unsubstituted alkylamine group is a substituted or unsubstituted C 1 -C 30 alkylamine group; the substituted or unsubstituted arylamine group is a substituted or unsubstituted C 6 -C 30 Arylamine group; the substituted or unsubstituted heteroarylamino group is a substituted or unsubstituted C 3 -C 30 heteroarylamino group.
  6. 如权利要求1-5任一项所述的化合物，其特征在于，所述除上述基团以外的含有O、N、S、B、P、F中至少一种杂原子的C1-C18的吸电子基团包括取代或未取代的酰亚胺基、取代或未取代的酰胺基、氰基、硝基或羟基。The compound according to any one of claims 1 to 5, characterized in that, in addition to the above-mentioned groups, the C 1 -C 18 containing at least one heteroatom among O, N, S, B, P and F The electron-withdrawing group includes a substituted or unsubstituted imide group, a substituted or unsubstituted amide group, a cyano group, a nitro group or a hydroxyl group.
  7. 如权利要求1-6任一项所述的化合物，其特征在于，所述R1、R2每次出现独立地为氢原子、氘原子、氚原子、卤素原子、氰基、金刚烷基、甲基、氘代甲基、氚代甲基、氟代丙基、三氟甲基、乙基、氘代乙基、氚代乙基、异丙基、氘代异丙基、氚代异丙基、叔丁基、氘代叔丁基、氚代叔丁基、苯基取代的叔丁基、环戊基、氘代环戊基、氚代环戊基、甲基取代的环戊基、环己基、苯基、氘代苯基、氚代苯基、二联苯基、氘代二联苯基、氚代二联苯基、三联苯基、氘代三联苯基、氚代三联苯基、二苯醚基、甲基取代的二苯醚基、萘基、蒽基、菲基、芘基、吡啶基、苯基取代的吡啶基、喹啉基、呋喃基、噻吩基、苯并呋喃基、二苯并呋喃基、叔丁基取代的二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、叔丁基取代的咔唑基、叔丁基取代的N-咔唑基苯基、9,9-二甲基芴基、螺芴基、甲基取代的苯基、乙基取代的苯基、异丙基取代的苯基、叔丁基取代的苯基、二联苯基、甲基取代的二联苯基、乙基取代的二联苯基、异丙基取代的二联苯基、叔丁基取代的二联苯基、氘代甲基取代的苯基、氘代乙基取代的苯基、氘代异丙基取代的苯基、氘代叔丁基取代的苯基、氘代甲基取代的二联苯基、氘代乙基取代的二联苯基、氘代异丙基取代的二联苯基、氘代叔丁基取代的二联苯基、苯基取代的氨基、叔丁基苯取代的氨基、叔丁基取代的二苯并呋喃基、苯基取代的叔丁基、氧杂蒽酮基、三嗪基、苯基取代的三嗪基、硼烷基、苯基取代的硼烷基、甲氧基或叔丁氧基。The compound according to any one of claims 1 to 6, wherein 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, Methyl, deuterated methyl, tritiated methyl, fluoropropyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl base, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, phenyl-substituted tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, Cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, diphenyl, deuterated diphenyl, tritiated diphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl , diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuran base, dibenzofuranyl, tert-butyl-substituted dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, tert-butyl-substituted carbazolyl, tert-butyl-substituted N-carbazolylphenyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl substituted phenyl, ethyl substituted phenyl, isopropyl substituted phenyl, tert-butyl substituted Phenyl, diphenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl substituted diphenyl, deuterated methyl Substituted phenyl, deuterated ethyl substituted phenyl, deuterated isopropyl substituted phenyl, deuterated tert-butyl substituted phenyl, deuterated methyl substituted diphenyl, deuterated ethyl substituted Diphenyl group, deuterated isopropyl substituted diphenyl group, deuterated tert-butyl substituted diphenyl group, phenyl substituted amino group, tert-butylbenzene substituted amino group, tert-butyl substituted diphenyl group Benzofuranyl, phenyl-substituted tert-butyl, xanthonyl, triazinyl, phenyl-substituted triazinyl, boralkyl, phenyl-substituted boralkyl, methoxy or tert-butoxy base.
  8. 如权利要求1-7任一项所述的化合物，其特征在于，相邻的所述R1连接成环时，所形成的环结构包括式(a)至式(i)所示的任意一种：
    The compound according to any one of claims 1 to 7, characterized in that when the adjacent R 1s are connected to form a ring, the ring structure formed includes any one of the formulas (a) to (i). kind:
    式(a)至式(i)中，*标记的位置为连接位置，式(a)至式(i)的结构通过*标记的位置以并环方式进行连接。In 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 *.
  9. 如权利要求3-8任一项所述的化合物，其特征在于，所述R2与邻近的所述R1连接成环时，所形成的环结构包括式(A)至式(D)所示的结构：
    The compound according to any one of claims 3 to 8, wherein when R 2 is connected to the adjacent R 1 to form a ring, the ring structure formed includes the formulas (A) to (D). The structure shown:
    式(A)中R5为氢原子、氘原子、氚原子、卤素原子、取代或未取代的烷基、取代或未取代的环烷基，n为0至4的整数；式(A)至式(D)中，*标记的位置为连接位置，式(A) 至式(D)的结构通过*标记的位置以并环方式进行连接。In the formula (A), 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), the position marked * is the connection position, formula (A) The structure to formula (D) is connected in a parallel ring manner through the positions marked with *.
  10. 如权利要求1-9所述的化合物，其特征在于，所述化合物包括结构式如式(1)-(268)所示的化合物中的任一种：















    The compound according to claims 1-9, characterized in that the compound includes any one of the compounds with structural formulas such as formulas (1)-(268):















  11. 如权利要求1-10任一项所述的化合物及其盐在电致发光器件、有机发光场效应晶体管、有机光伏器件、发光电化学电池、光电转换器、开光器件、图像传感器、激光器、感光器件、生物成像设备、涂料、有机激光设备中的应用。The compound and its salt according to any one of claims 1 to 10 can be used in electroluminescent devices, organic light-emitting field effect transistors, organic photovoltaic devices, luminescent electrochemical cells, photoelectric converters, light-operating devices, image sensors, lasers, and photosensitive devices. Applications in devices, bioimaging equipment, coatings, and organic laser equipment.
  12. 一种发光层，其特征在于，所述发光层包括权利要求1-10任一项所述的化合物。A luminescent layer, characterized in that the luminescent layer includes the compound according to any one of claims 1-10.
  13. 如权利要求12所述的发光层，其特征在于，所述发光层包括主体材料和掺杂材料，所述掺杂材料包括所述化合物。The light-emitting layer of claim 12, wherein the light-emitting layer includes a host material and a doping material, and the doping material includes the compound.
  14. 一种电子器件，其特征在于，所述电子器件包括权利要求1-10任一项所述的化合物； 或者包括权利要求12-13任一项所述的发光层。An electronic device, characterized in that the electronic device includes the compound described in any one of claims 1-10; Or it includes the luminescent layer according to any one of claims 12-13.
  15. 如权利要求14所述的电子器件，其特征在于，所述电子器件包括阴极和阳极，以及位于所述阴极和所述阳极之间的功能层，所述功能层包括所述化合物。The electronic device of claim 14, wherein the electronic device includes a cathode and an anode, and a functional layer located between the cathode and the anode, the functional layer including the compound.
  16. 如权利要求14或15所述的电子器件，其特征在于，所述电子器件包括电致发光器件、有机发光场效应晶体管、有机光伏器件或发光电化学电池。The electronic device according to claim 14 or 15, characterized in that the electronic device includes an electroluminescent device, an organic light-emitting field effect transistor, an organic photovoltaic device or a light-emitting electrochemical cell.
  17. 一种显示装置，其特征在于，所述显示装置包括权利要求14-16任一项所述的电子器件；或者包括权利要求12-13任一项所述的发光层。A display device, characterized in that the display device includes the electronic device according to any one of claims 14-16; or includes the light-emitting layer according to any one of claims 12-13.
  18. 一种电子设备，其特征在于，所述电子设备包括权利要求17所述的显示装置；或者包括权利要求14-16任一项所述的电子器件。An electronic device, characterized in that the electronic device includes the display device according to claim 17; or the electronic device according to any one of claims 14-16.
  19. 一种照明装置，其特征在于，所述照明装置包括权利要求14-16任一项所述的电子器件；或者包括权利要求12-13任一项所述的发光层。 A lighting device, characterized in that the lighting device includes the electronic device according to any one of claims 14-16; or includes the luminescent layer according to any one of claims 12-13.
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