WO2022205587A1 - 有机化合物及其制作方法、显示面板 - Google Patents

有机化合物及其制作方法、显示面板 Download PDF

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WO2022205587A1
WO2022205587A1 PCT/CN2021/095380 CN2021095380W WO2022205587A1 WO 2022205587 A1 WO2022205587 A1 WO 2022205587A1 CN 2021095380 W CN2021095380 W CN 2021095380W WO 2022205587 A1 WO2022205587 A1 WO 2022205587A1
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organic compound
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白科研
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武汉华星光电半导体显示技术有限公司
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Priority to US17/419,690 priority Critical patent/US20230174494A1/en
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Definitions

  • the present application relates to the field of display, and in particular, to an organic compound, a method for making the same, and a display panel.
  • OLED organic light-emitting diodes, organic light-emitting diodes
  • Embodiments of the present application provide an organic compound, a manufacturing method thereof, and a display panel to alleviate the technical problem of low mobility of light-emitting device layer materials.
  • the embodiments of the present application provide an organic compound, and the organic compound is represented by the following general formula:
  • the Ar includes any one or a combination of hydrogen and hydrogen isotopes, aromatic groups, arylamine groups, heteroarylamine groups and condensed ring groups, and the R 1 or the The R 2 is independently any one or a combination of any one of alkyl, alkoxy, heteroalkyl and aromatic groups.
  • the Ar includes protium, deuterium, tritium, an aromatic group with 6 to 60 carbon atoms, an arylamine group with 6 to 60 carbon atoms, and a heterocyclic group with 6 to 60 carbon atoms.
  • a combination of any one or more of an arylamine group and a fused ring group with 10 to 60 carbon atoms, the R 1 or the R 2 is an alkyl group with 1 to 22 carbon atoms, a carbon Any one or a combination of any one or more of an alkoxy group having 1 to 22 atoms, a heteroalkyl group having 1 to 22 carbon atoms, and an aromatic group having 6 to 60 carbon atoms.
  • the Ar is an axisymmetric group containing a benzene ring.
  • the Ar is a combination of any one or more of the following:
  • the aromatic group includes an oxygen-containing aromatic group or a silicon-containing aromatic group
  • the aromatic amine group includes an oxygen-containing aromatic amine group or a silicon-containing arylamine group
  • the fused ring group includes any one of naphthalene, anthracene, and pyrene.
  • the Ar is a combination of any one or more of the following:
  • the R 1 or the R 2 are each independently any one of methyl, ethyl or phenyl.
  • the structural formula of the organic compound is:
  • the Ar is an aromatic group with 6-60 carbon atoms or a heteroaromatic group with 6-60 carbon atoms.
  • the structure of the organic compound includes any one or more of the following combinations:
  • the embodiment of the present application also provides a method for making an organic compound, comprising:
  • the first substance and the second substance are mixed to form the organic compound represented by the general formula (1):
  • the first substance is represented by the general formula (2):
  • the R 1 or the R 2 are independently any one or a combination of an alkyl group, an alkoxy group, a heteroalkyl group and an aromatic group
  • the X is a halogen
  • the second Substances include any one or more combinations of aromatic groups, arylamine groups, heteroarylamine groups and condensed ring groups
  • the Ar includes hydrogen and isotopes of the hydrogen, aromatic groups, A combination of any one or more of arylamine groups, heteroarylamine groups and fused ring groups.
  • the molar ratio of the first substance to the second substance is 1:1 to 1:3.
  • the embodiments of the present application also provide a display panel, which includes a light-emitting device layer, and the light-emitting device layer has an organic compound, and the organic compound is represented by the following general formula:
  • the Ar includes any one or a combination of hydrogen and hydrogen isotopes, aromatic groups, arylamine groups, heteroarylamine groups and condensed ring groups, and the R 1 or the The R 2 is independently any one or a combination of any one of alkyl, alkoxy, heteroalkyl and aromatic groups.
  • the Ar includes protium, deuterium, tritium, an aromatic group with 6 to 60 carbon atoms, an arylamine group with 6 to 60 carbon atoms, and a heterocyclic group with 6 to 60 carbon atoms.
  • a combination of any one or more of an arylamine group and a fused ring group with 10 to 60 carbon atoms, the R 1 or the R 2 is an alkyl group with 1 to 22 carbon atoms, a carbon Any one or a combination of any one or more of an alkoxy group having 1 to 22 atoms, a heteroalkyl group having 1 to 22 carbon atoms, and an aromatic group having 6 to 60 carbon atoms.
  • the Ar is an axisymmetric group containing a benzene ring.
  • the Ar is a combination of any one or more of the following:
  • the aromatic group includes an oxygen-containing aromatic group or a silicon-containing aromatic group
  • the aromatic amine group includes an oxygen-containing aromatic amine group or a silicon-containing arylamine group
  • the fused ring group includes any one of naphthalene, anthracene, and pyrene.
  • the Ar is a combination of any one or more of the following:
  • the R 1 or the R 2 are each independently any one of methyl, ethyl or phenyl.
  • the structural formula of the organic compound is:
  • the Ar is an aromatic group with 6-60 carbon atoms or a heteroaromatic group with 6-60 carbon atoms.
  • the structure of the organic compound includes any one or more of the following combinations:
  • an organic compound with high mobility is obtained by coordinating with other groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • FIG. 1 is a schematic structural diagram of a display panel provided by an embodiment of the present invention.
  • FIG. 2 is a schematic structural diagram of a display device provided by an embodiment of the present invention.
  • the present application provides an organic compound, a method for producing the same, and a display panel.
  • a display panel In order to make the purpose, technical solution and effect of the present application more clear and definite, the present application is further described in detail below with reference to the accompanying drawings and examples. It should be understood that the specific embodiments described herein are only used to explain the present application, but not to limit the present application.
  • Embodiments of the present application provide an organic compound, a manufacturing method thereof, and a display panel. Detailed descriptions are given below. It should be noted that the description order of the following embodiments is not intended to limit the preferred order of the embodiments.
  • the embodiment of the present invention provides an organic compound, and the organic compound is represented by the following general formula:
  • the Ar includes any one or a combination of hydrogen and hydrogen isotopes, aromatic groups, arylamine groups, heteroarylamine groups and condensed ring groups, and the R 1 or the The R 2 is independently any one or a combination of any one of alkyl, alkoxy, heteroalkyl and aromatic groups.
  • an organic compound with high mobility is obtained by coordinating with other groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • the organic compound is represented by the following general formula:
  • the general junction formula is the general structural formula of the phenazine-like fluorene structure.
  • the R 1 , the R 2 and the Ar may all be electron donating groups.
  • the R 1 , the R 2 and the Ar may all be electron donating groups.
  • the Ar includes any one or a combination of hydrogen and the isotope of the hydrogen, an aromatic group, an arylamine group, a heteroarylamine group and a condensed ring group, and the R 1 or the R 2 are each independently any one or a combination of any one or more of alkyl, alkoxy, heteroalkyl and aromatic groups.
  • the Ar has the effect of adjusting the transmission efficiency, and the R 1 or the R 2 is used to assist in adjusting the transmission efficiency.
  • the R 1 or the R 2 is an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, a heteroalkyl group having 1 to 22 carbon atoms, or An aromatic group with 6 to 60 carbon atoms
  • the Ar includes protium, deuterium, tritium, an aromatic group with 6 to 60 carbon atoms, an arylamine group with 6 to 60 carbon atoms, and an aromatic group with 6 to 60 carbon atoms.
  • the organic compound may be used for evaporation materials
  • C is a carbon atom
  • the molecular weight required for mass production of vapor deposition molecules is less than 1000.
  • the Ar includes a nitrogen-containing aromatic group or a nitrogen-containing heteroaromatic group, wherein the nitrogen element can make the organic compound have strong electron donating ability and improve the mobility performance of the organic compound .
  • the Ar is an axisymmetric group containing a benzene ring.
  • the axisymmetric group containing a benzene ring can enhance the stability of the organic compound through the axis symmetry of the group.
  • the aromatic group includes an oxygen-containing aromatic group or a silicon-containing aromatic group
  • the arylamine group includes an oxygen-containing arylamine group or a silicon-containing arylamine group
  • the fused ring group Including any one of naphthalene, anthracene, and pyrene.
  • the addition of silicon element or oxygen element can improve the electron donating ability of the organic compound and improve the mobility performance of the organic compound.
  • the R 1 or the R 2 are each independently any one of methyl, ethyl or phenyl.
  • the organic compound may be used as an evaporation material, and the molecular weight of methyl group, ethyl group or phenyl group is relatively low, which is favorable for evaporation and simple in synthesis.
  • the Ar is any one or more of the following combinations:
  • the Ar adjusts the mobility of the organic compound through groups with different molecular weights, improves the stability of the organic compound through symmetrical groups, and improves the stability of the organic compound through nitrogen- and oxygen-containing groups.
  • the mobility of the organic matter can be improved, and the molecular weight can be effectively adjusted.
  • nitrogen and oxygen can form intermolecular and intramolecular hydrogen bonds, thereby further improving the stability of the organic matter.
  • the structural formula of the organic compound is:
  • the Ar is an aromatic group with 6-60 carbon atoms or a heteroaromatic group with 6-60 carbon atoms. It can be seen that the R 1 and the R 2 are both methyl groups, and the methyl group has a low molecular weight, which is further conducive to evaporation and reduces the difficulty of synthesis. The main design direction is concentrated on the Ar, and the Mobility performance.
  • the structure of the organic compound includes any one or more of the following combinations:
  • the HOMO electrochemical energy level of Compound 1 is -5.58 eV, and the LUMO electrochemical energy level is -2.43 eV.
  • the HOMO electrochemical energy level of compound 2 is -5.61 eV, and the LUMO electrochemical energy level is -2.45 eV.
  • the HOMO electrochemical energy level of compound 3 is -5.66 eV, and the LUMO electrochemical energy level is -2.44 eV. It can be seen that, taking three structures as examples, the characterization parameters of the organic compounds can be used for transport materials.
  • an organic compound with high mobility is obtained by coordinating with other groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • the embodiment of the present invention also provides a method for making an organic compound, comprising:
  • the first substance is represented by the general formula (2):
  • the R 1 or the R 2 are independently any one or a combination of an alkyl group, an alkoxy group, a heteroalkyl group and an aromatic group
  • the X is a halogen
  • the second Substances include any one or more combinations of aromatic groups, arylamine groups, heteroarylamine groups and condensed ring groups
  • the Ar includes hydrogen and isotopes of the hydrogen, aromatic groups, A combination of any one or more of arylamine groups, heteroarylamine groups and fused ring groups.
  • an organic compound with high mobility is obtained by coordinating with other groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • the preparation method of the organic compound comprising:
  • the first substance is represented by the general formula (2):
  • the R 1 , the R 2 and the Ar may all be electron donating groups.
  • the R 1 , the R 2 and the Ar may all be electron donating groups.
  • the Ar includes any one or a combination of hydrogen and the isotope of the hydrogen, an aromatic group, an arylamine group, a heteroarylamine group and a condensed ring group, and the R 1 or the R 2 are each independently any one or a combination of any one or more of alkyl, alkoxy, heteroalkyl and aromatic groups.
  • the Ar has the effect of adjusting the transmission efficiency, and the R 1 or the R 2 is used to assist in adjusting the transmission efficiency.
  • the R 1 or the R 2 are independently any one or a combination of any one or more of an alkyl group, an alkoxy group, a heteroalkyl group and an aromatic group
  • the X is a halogen
  • the The second substance includes a combination of any one or more groups in an aromatic group, an arylamine group, a heteroarylamine group and a condensed ring group
  • the Ar includes an aromatic group, an arylamine group, A combination of any one or more of heteroarylamine groups and fused ring groups.
  • the second substance further includes a dehalogenation hydrogenation agent, or the X in the first substance is hydrogen.
  • the dehalogenation hydrogenation agent may include LiAlH 4 , or tri-tert-butylstannane, or a soluble organic polymer-supported palladium complex as a catalyst for hydrogenation dehalogenation in an inorganic alkaline environment.
  • the X is bromine, iodine or chlorine.
  • the synthesis efficiency the synthesis efficiency of bromine and iodine is higher, and in the cost calculation, the cost of chlorine is lower.
  • the R 1 or the R 2 is an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, a heteroalkyl group having 1 to 22 carbon atoms, or An aromatic group with 6 to 60 carbon atoms
  • the Ar includes protium, deuterium, tritium, an aromatic group with 6 to 60 carbon atoms, an arylamine group with 6 to 60 carbon atoms, and an aromatic group with 6 to 60 carbon atoms.
  • the organic compound may be used for evaporation materials
  • C is a carbon atom
  • the molecular weight required for mass production of vapor deposition molecules is less than 1000.
  • the Ar includes a nitrogen-containing aromatic group or a nitrogen-containing heteroaromatic group, wherein the nitrogen element can make the organic compound have strong electron donating ability and improve the mobility performance of the organic compound .
  • the Ar is an axisymmetric group containing a benzene ring.
  • the axisymmetric group containing a benzene ring can enhance the stability of the organic compound through the axis symmetry of the group.
  • the aromatic group includes an oxygen-containing aromatic group or a silicon-containing aromatic group
  • the arylamine group includes an oxygen-containing arylamine group or a silicon-containing arylamine group
  • the fused ring group Including any one of naphthalene, anthracene, and pyrene.
  • the addition of silicon element or oxygen element can improve the electron donating ability of the organic compound and improve the mobility performance of the organic compound.
  • the R 1 or the R 2 are each independently any one of methyl, ethyl or phenyl.
  • the organic compound may be used as an evaporation material, and the molecular weight of methyl group, ethyl group or phenyl group is relatively low, which is favorable for evaporation and simple in synthesis.
  • the Ar is any one or more of the following combinations:
  • the Ar adjusts the mobility of the organic compound through groups with different molecular weights, improves the stability of the organic compound through symmetrical groups, and improves the stability of the organic compound through nitrogen- and oxygen-containing groups.
  • the mobility of the organic matter can be improved, and the molecular weight can be effectively adjusted.
  • nitrogen and oxygen can form intermolecular and intramolecular hydrogen bonds, thereby further improving the stability of the organic matter.
  • the structural formula of the organic compound is:
  • the Ar is an aromatic group with 6-60 carbon atoms or a heteroaromatic group with 6-60 carbon atoms. It can be seen that the R 1 and the R 2 are both methyl groups, and the methyl group has a low molecular weight, which is further conducive to evaporation and reduces the difficulty of synthesis. The main design direction is concentrated on the Ar, and the Mobility performance.
  • the structural formula of the first substance is:
  • the second substance includes any one or more of the following groups in combination:
  • step S100 is performed in an inert gas environment, and the inert gas environment can be argon or helium, which can protect the stability of the organic compound and the efficiency of synthesis.
  • step S100 includes:
  • step S110 is to mix the first substance and the second substance in a molar ratio of 1:1.2 to form a first mixture.
  • Properly increasing the ratio of the second substance can improve the utilization rate of the first substance.
  • the reaction can be It is sufficient, and it can avoid excessive waste of the second substance or excessive impurities in the product, resulting in substandard product purity.
  • the catalyst can speed up step S100 to improve the production efficiency of the organic compound.
  • the catalyst can be palladium acetate, which can speed up the reaction without destroying the performance of the organic compound, and it is easier to separate palladium acetate in the later stage, which is convenient and quick, and speeds up the reaction production efficiency.
  • the ratio of the substance amount of the catalyst to the substance amount of the first substance is 1:20 ⁇ 1:30.
  • the ratio of the amount of the material of the catalyst to the amount of the first material is 1:25. This content can not only ensure the catalytic efficiency, but also facilitate the separation and improve the production when the catalyst is purified and separated in the later stage. efficiency.
  • the ligand can be used to protect other functional groups or stabilize some easily reactive compounds, such as the aromatic group, arylamine group, heteroarylamine group and fused ring group of the second substance any one or more of the groups, and the R 1 or the R 2 in the first species, and the nitrogen heterocycle in the first species.
  • the ligand can be tri-tert-butylphosphine tetrafluoroborate, and tri-tert-butylphosphine tetrafluoroborate is used as the ligand, and the reaction conditions do not need to add precious silver salt, which can save The steps speed up the synthesis of complex polyaromatic compounds, make the reaction more green and environmentally friendly, and have a high atom utilization rate, which reflects the concept of green chemistry now advocated, and is also helpful for functional group compatibility and reaction efficiency.
  • the ratio of the amount of the substance of the ligand to the amount of the substance of the second substance is 1:8 to 1:12.
  • the ratio of the amount of the ligand to the amount of the second material is 1:10. This content can not only ensure that the group protecting the second material will not be damaged, but also The excessive content of the ligand can be prevented from inhibiting the progress of the reaction, thereby ensuring the efficiency of the reaction production.
  • the alkali is used to provide an alkaline environment.
  • the base can be NaOt-Bu, and NaOt-Bu can not only provide an alkaline environment, but also have a certain catalytic effect to speed up the production efficiency of the organic compound.
  • the ratio of the amount of the alkali substance to the amount of the second substance is 1:0.8 ⁇ 1:1.2.
  • the ratio of the amount of the alkali substance to the amount of the second substance is 1:1, and this content can not only ensure the existence of an alkaline environment, but also increase a certain reaction rate, ensuring that the reaction The efficiency of production, and at the same time, because the alkali environment is too high, the organic compound is too viscous, which is inconvenient for the operation of the subsequent steps.
  • steps S110 to S150 may be performed simultaneously.
  • the third mixture is placed in ice water for extraction and the organic phases are combined to form a fourth mixture.
  • the extractant in step S180 may be dichloromethane.
  • the column chromatography agent for column chromatography can be dichloromethane: n-hexane in a volume ratio of 1:1 to 1:10.
  • the column chromatography agent of the column chromatography can be dichloromethane: n-hexane with a volume ratio of 1:5. It can achieve a good separation effect without excessive waste and save production costs.
  • the structure of the organic compound includes any one or more of the following combinations:
  • the HOMO electrochemical energy level of Compound 1 is -5.58 eV, and the LUMO electrochemical energy level is -2.43 eV.
  • the HOMO electrochemical energy level of compound 2 is -5.61 eV, and the LUMO electrochemical energy level is -2.45 eV.
  • the HOMO electrochemical energy level of compound 3 is -5.66 eV, and the LUMO electrochemical energy level is -2.44 eV. It can be seen that, taking three structures as examples, the characterization parameters of the organic compounds can be used for transport materials.
  • reaction formula of compound 1 is as follows:
  • the steps of the preparation method of compound 1 can be exemplified by adding raw material 1 (2.92 g, 5 mmol), carbazole (1.00 g, 6 mmol), palladium acetate (45 mg, 0.2 mmol) and trisodium chloride into a 250 mL two-necked flask.
  • tert-butylphosphine tetrafluoroborate (0.17 g, 0.6 mmol)
  • NaOt-Buu 0.58 g, 6 mmol
  • reaction formula of compound 2 is as follows:
  • the steps of the preparation method of compound 2 can be exemplified by adding raw material 1 (2.92g, 5mmol), phenoxazine (1.10g, 6mmol), palladium acetate (45mg, 0.2mmol) and Tri-tert-butylphosphine tetrafluoroborate (0.17 g, 0.6 mmol), then NaOt-Buu (0.58 g, 6 mmol) was added to the glove box, and 100 mL of toluene that had been dewatered and deoxygenated in advance was added under argon atmosphere, The reaction was carried out at 120°C for 24 hours.
  • reaction formula of compound 3 is as follows:
  • the steps of the preparation method of compound 3 can be exemplified by adding raw material 1 (2.92g, 5mmol), 9,9'-dimethylacridine (1.26g, 6mmol), palladium acetate into a 250mL two-necked flask (45 mg, 0.2 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.17 g, 0.6 mmol), then NaOt-Buu (0.58 g, 6 mmol) was added to the glove box, and 100 mL of preliminarily injected under argon atmosphere Toluene dehydrated and deoxygenated was reacted at 120°C for 24 hours.
  • the embodiment of the present invention enhances the display performance of the display device by coordinating with other groups on the basis of the structure of the phenazine difluorene to obtain an organic compound with high mobility.
  • An embodiment of the present invention further provides a display panel 100, including a light-emitting device layer 500, and the light-emitting device layer 500 includes any of the above-mentioned organic compounds or the organic compounds produced according to any of the above-mentioned organic compounds. compound.
  • an organic compound with high mobility is obtained by coordinating with other groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • the display panel 100 includes a substrate 200, an array substrate 300 on the substrate 200, and a light-emitting device layer 500 on the array substrate 300, the light-emitting device layer 500 comprising any of the above-mentioned organic compounds or
  • the organic compound prepared according to any of the above-mentioned methods for preparing an organic compound please refer to FIG. 1 for details.
  • the array substrate 300 includes an active layer, a first insulating layer on the active layer, a gate layer on the first insulating layer, and a first insulating layer on the gate layer. Two insulating layers, a source-drain layer on the second insulating layer, and a third insulating layer on the source-drain layer.
  • the display panel 100 further includes an anode layer 410 on a side close to the array substrate 300 , a light emitting device layer 500 on the anode layer 410 , and a cathode layer 420 on the light emitting device layer 500 and the light coupling output layer 430 located on the cathode layer 420 , please refer to FIG. 1 for details.
  • the light emitting device layer 500 includes a hole injection layer 510 located on the anode layer 410 , a hole transport layer 520 located on the hole injection layer 510 , and a hole transport layer 520 located on the hole transport layer 520 .
  • the material in the light-emitting material layer 540 may be OLED or QLED (Quantum Dot Light Emitting Diodes, quantum dot light-emitting diode), which is not limited herein.
  • the anode layer 410 includes a first ITO (indium tin oxide) layer, a silver layer on the first ITO layer, and a second ITO layer on the silver layer.
  • the anode layer 410 It is a totally reflective electrode, which can improve the light extraction efficiency of the light emitting device layer 500 .
  • the cathode layer 420 is a transparent electrode material or a semi-transparent electrode material, which may include ITO, so as to increase the light extraction efficiency of the light emitting device layer 500 .
  • the light coupling output layer 430 is used to improve the light extraction efficiency of the light emitting device layer 500 and enhance the display effect.
  • the hole transport layer 520 includes the organic compound.
  • the hole transport efficiency can be best improved.
  • the HOMO electrochemical energy level of compound 1 is -5.58 eV
  • the LUMO electrochemical energy level is -2.43 eV
  • the HOMO electrochemical energy level of compound 2 is -5.61 eV
  • the LUMO electrochemical energy level is -2.45 eV
  • the HOMO electrochemical energy level of compound 3 is -5.66 eV
  • the LUMO electrochemical energy level is -2.44 eV.
  • compound 1, compound 2 and compound 3 are used for the hole transport layer 520 .
  • the highest current efficiency of the display panel 100 including the hole transport layer 520 of the compound 1 is 40.1 cd/A, and the color coordinates (CIEx, CIEy) for red light are (0.685, 0.291) , the maximum external quantum efficiency is 36.7%.
  • the highest current efficiency of the display panel 100 including the hole transport layer 520 of the compound 2 is 36.8cd/A, and the color coordinates (CIEx, CIEy) for red light are (0.684, 0.290) , the maximum external quantum efficiency is 34.3%.
  • the highest current efficiency of the display panel 100 including the hole transport layer 520 of the compound 3 is 39.8cd/A, and the color coordinates (CIEx, CIEy) for red light are (0.686, 0.292) , the maximum external quantum efficiency is 35.5%.
  • the organic compounds in the embodiment of the present invention taking Compound 1, Compound 2, and Compound 3 as examples, can be used as the hole transport layer 520 and have high current efficiency, and higher maximum external quantum efficiency, and at the same time, the emission color of red light is also calibrated.
  • the organic compound in the embodiment of the present invention can be used as the material of the light-emitting device layer 500, especially as the material of the hole transport layer 520. The better working performance prolongs the service life of the display panel 100 .
  • an organic compound with high mobility is obtained by adding other electron donating groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • Embodiments of the present invention further provide a display device 10, including the display panel 100 as described above.
  • the display device 10 further includes an encapsulation layer 20 and a cover layer 30 on the display panel 100 , please refer to FIG. 2 for details.
  • an organic compound with high mobility is obtained by adding other electron donating groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.
  • Embodiments of the present invention disclose an organic compound, a manufacturing method thereof, and a display panel.
  • the organic compound is represented by the following general formula:
  • the Ar includes any one or a combination of hydrogen and the isotope of the hydrogen, aromatic group, arylamine group, heteroarylamine group and condensed ring group
  • the R 1 or the R 2 Each independently is a combination of any one or more of alkyl, alkoxy, heteroalkyl and aromatic groups.
  • an organic compound with high mobility is obtained by coordinating with other groups on the basis of the structure of the phenazine difluorene, thereby enhancing the display performance of the display device.

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Abstract

本发明实施例公开了一种有机化合物及其制作方法、显示面板；有机化合物通式为（I）；Ar包括氢及氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，R1或R2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合；通过吩嗪连芴结构与其他基团配合，得到高迁移率的有机化合物。

Description

有机化合物及其制作方法、显示面板 技术领域
本申请涉及显示领域，尤其涉及一种有机化合物及其制作方法、显示面板。
背景技术
近些年，OLED(organic light-emitting diodes，有机电致发光二极管)显示面板越来越受到市场青睐。
目前，在OLED显示面板中，发光器件层材料的能级以及迁移率一直存在矛盾的关系，开发匹配能级以及高迁移率的发光器件层材料迫在眉睫。
因此，亟需一种有机化合物及其制作方法、显示面板以解决上述技术问题。
技术问题
本申请实施例提供一种有机化合物及其制作方法、显示面板，以缓解发光器件层材料的迁移率低的技术问题。
技术解决方案
为解决上述问题，本申请提供的技术方案如下：
本申请实施例提供了一种有机化合物，所述有机化合物如下述通式表示：
Figure PCTCN2021095380-appb-000001
其中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。
在一实施例中，所述Ar包括氕、氘、氚、碳原子数为6～60的芳香基团、碳原子数为6～60的芳胺基团、碳原子数为6～60的杂芳胺基团及碳原子数为10～60的稠环基团中的任意一种或多种的组合，所述R 1或所述R 2为碳原子数为1～22的烷基、碳原子数为1～22的烷氧基、碳原子数为1～22的杂烷基及碳原子数为6～60的芳香基团中的任意一种或多种的组合。
在一实施例中，所述Ar为含苯环的轴对称基团。
在一实施例中，所述Ar为以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000002
Figure PCTCN2021095380-appb-000003
在一实施例中，所述芳香基团包括含氧芳香基团或含硅芳香基团，所述芳胺基团包括含氧芳胺基团或含硅芳胺基团，所述稠环基团包括萘、蒽、芘中的任意一种。
在一实施例中，所述Ar为以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000004
Figure PCTCN2021095380-appb-000005
在一实施例中，所述R 1或所述R 2分别独立的为甲基、乙基或苯基中的任一种。
在一实施例中，所述有机化合物的结构式为：
Figure PCTCN2021095380-appb-000006
其中，所述Ar为碳原子数为6～60的芳香基团或碳原子数为6～60的杂芳 香基团。
在一实施例中，所述有机化合物的结构包括以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000007
Figure PCTCN2021095380-appb-000008
Figure PCTCN2021095380-appb-000009
本申请实施例还提供了一种有机化合物的制作方法，包括：
将第一物质与第二物质混合，形成所述有机化合物，所述有机化合物由通式(1)表示：
Figure PCTCN2021095380-appb-000010
所述第一物质由通式(2)表示：
Figure PCTCN2021095380-appb-000011
其中，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合，所述X为卤素，所述第二物质包括芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种基团的组合，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合。
在一实施例中，所述第一物质与所述第二物质的摩尔比为1:1至1:3。
本申请实施例还提供了一种显示面板，其中，包括发光器件层，所述发光器件层有机化合物，所述有机化合物如下述通式表示：
Figure PCTCN2021095380-appb-000012
其中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为 烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。
在一实施例中，所述Ar包括氕、氘、氚、碳原子数为6～60的芳香基团、碳原子数为6～60的芳胺基团、碳原子数为6～60的杂芳胺基团及碳原子数为10～60的稠环基团中的任意一种或多种的组合，所述R 1或所述R 2为碳原子数为1～22的烷基、碳原子数为1～22的烷氧基、碳原子数为1～22的杂烷基及碳原子数为6～60的芳香基团中的任意一种或多种的组合。
在一实施例中，所述Ar为含苯环的轴对称基团。
在一实施例中，所述Ar为以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000013
Figure PCTCN2021095380-appb-000014
在一实施例中，所述芳香基团包括含氧芳香基团或含硅芳香基团，所述芳胺基团包括含氧芳胺基团或含硅芳胺基团，所述稠环基团包括萘、蒽、芘中的任意一种。
在一实施例中，所述Ar为以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000015
Figure PCTCN2021095380-appb-000016
Figure PCTCN2021095380-appb-000017
在一实施例中，所述R 1或所述R 2分别独立的为甲基、乙基或苯基中的任一种。
在一实施例中，所述有机化合物的结构式为：
Figure PCTCN2021095380-appb-000018
其中，所述Ar为碳原子数为6～60的芳香基团或碳原子数为6～60的杂芳香基团。
在一实施例中，所述有机化合物的结构包括以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000019
Figure PCTCN2021095380-appb-000020
Figure PCTCN2021095380-appb-000021
有益效果
本发明实施例通过在吩嗪连芴的结构基础上，与其他基团配合，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
附图说明
图1是本发明实施例提供的显示面板的结构示意图；
图2是本发明实施例提供的显示装置的结构示意图。
本发明的实施方式
本申请提供一种有机化合物及其制作方法、显示面板，为使本申请的目的、技术方案及效果更加清楚、明确，以下参照附图并举实施例对本申请进一步详细说明。应当理解，此处所描述的具体实施例仅用以解释本申请，并不用于限定本申请。
本申请实施例提供一种有机化合物及其制作方法、显示面板。以下分别进 行详细说明。需说明的是，以下实施例的描述顺序不作为对实施例优选顺序的限定。
本发明实施例提供了一种有机化合物，所述有机化合物如下述通式表示：
Figure PCTCN2021095380-appb-000022
其中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。
本发明实施例通过在吩嗪连芴的结构基础上，与其他基团配合，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
现结合具体实施例对本发明的技术方案进行描述。
所述有机化合物如下述通式表示：
Figure PCTCN2021095380-appb-000023
本实施例中，该结通式为类吩嗪连芴结构的结构通式。
本实施例中，所述R 1、所述R 2及所述Ar可以均为给电子基团。通过在吩嗪连芴强的给电子能力，搭配其他给电子基团，得到具有高迁移率的化合物，所述化合物可以制作成传输材料，以用于发光材料中，增强显示设备的显示效能。
本实施例中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。所述Ar有调节传输效率的作用，所述R 1或所述R 2用于辅助调节传输效率。
本实施例中，所述R 1或所述R 2为碳原子数为1～22的烷基、碳原子数为1～22的烷氧基、碳原子数为1～22的杂烷基或碳原子数为6～60的芳香基团，所述Ar包括氕、氘、氚、碳原子数为6～60的芳香基团、碳原子数为6～60的 芳胺基团、碳原子数为6～60的杂芳胺基团及碳原子数为10～60的稠环基团中的任意一种或多种的组合，所述有机化合物可能用于蒸镀材料，C为碳原子，C数越多，分子量越大，越不利于蒸镀，量产蒸镀分子要求分子量为小于1000。
本实施例中，所述Ar包括含氮的芳香基团或含氮的杂芳香基团，其中氮元素可以使所述有机化合物具有较强的给电子能力，提高所述有机化合物的迁移率性能。
本实施例中，所述Ar为含苯环的轴对称基团。含苯环的轴对称基团可以通过基团的轴对称性，加强所述有机化合物的稳定性。
本实施例中，所述芳香基团包括含氧芳香基团或含硅芳香基团，所述芳胺基团包括含氧芳胺基团或含硅芳胺基团，所述稠环基团包括萘、蒽、芘中的任意一种。硅元素或氧元素的加入，可以提高所述有机化合物的给电子能力，提高所述有机化合物的迁移率性能。
本实施例中，所述R 1或所述R 2分别独立的为甲基、乙基或苯基中的任一种。所述有机化合物可能用于蒸镀材料，甲基、乙基或苯基的分子量较低，有利于蒸镀，且合成简单。
本实施例中，所述Ar为以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000024
Figure PCTCN2021095380-appb-000025
本实施例中，所述Ar通过不同分子量的基团来调节所述有机化合物的迁移率性能，通过对称性的基团提升所述有机物的稳定性；通过含氮、氧的基团，提升所述有机物的迁移率性能，并且可以有效调节分子量，同时，氮氧可以形成分子间与分子内氢键，进一步提高所述有机物的稳定性。
本实施例中，所述有机化合物的结构式为：
Figure PCTCN2021095380-appb-000026
其中，所述Ar为碳原子数为6～60的芳香基团或碳原子数为6～60的杂芳香基团。可以看出，所述R 1及所述R 2均为甲基，甲基是分子量低，进一步有利于蒸镀，降低合成难度，将主要设计方向集中于所述Ar，提高所述有机化合物的迁移率性能。
本实施例中，所述有机化合物的结构包括以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000027
Figure PCTCN2021095380-appb-000028
Figure PCTCN2021095380-appb-000029
以
Figure PCTCN2021095380-appb-000030
Figure PCTCN2021095380-appb-000031
为例，三种化合物分别命名为化合物1、化合物2以及化合物3。
本实施例中，化合物1的HOMO电化学能级为-5.58eV，LUMO电化学能级为-2.43eV。化合物2的HOMO电化学能级为-5.61eV，LUMO电化学能级为-2.45eV。化合物3的HOMO电化学能级为-5.66eV，LUMO电化学能级为-2.44eV。可以看出，以三种结构为例，所述有机化合物的表征参数可以用于传输材料。
本发明实施例通过在吩嗪连芴的结构基础上，与其他基团配合，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
本发明实施例还提供了一种有机化合物的制作方法，包括：
S100、将第一物质与第二物质混合，形成所述有机化合物，所述有机化合物由通式(1)表示：
Figure PCTCN2021095380-appb-000032
所述第一物质由通式(2)表示：
Figure PCTCN2021095380-appb-000033
其中，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合，所述X为卤素，所述第二物质包括芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种基团的组合，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合。
本发明实施例通过在吩嗪连芴的结构基础上，与其他基团配合，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
现结合具体实施例对本发明的技术方案进行描述。
所述有机化合物的制作方法，包括：
S100、将第一物质与第二物质混合，形成所述有机化合物，所述有机化合物由通式(1)表示：
Figure PCTCN2021095380-appb-000034
所述第一物质由通式(2)表示：
Figure PCTCN2021095380-appb-000035
本实施例中，所述R 1、所述R 2及所述Ar可以均为给电子基团。通过在吩嗪连芴强的给电子能力，搭配其他给电子基团，得到具有高迁移率的化合物，所述化合物可以制作成传输材料，以用于发光材料中，增强显示设备的显示效能。
本实施例中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。所述Ar有调节传输效率的作用，所述R 1或所述R 2用于辅助调节传输效率。
本实施例中，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合，所述X为卤素，所述第二物质包括芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种基团的组合，所述Ar包括芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合。
本实施例中，所述第二物质还包括脱卤加氢剂，或者所述第一物质中的所述X为氢。
本实施例中，所述脱卤加氢剂可以包括LiAlH 4、或三叔丁基锡烷，或者无机碱性环境中搭配可溶性有机高分子负载钯络合物作催化剂加氢脱卤。
本实施例中，所述X为溴或碘或氯。在合成效率中，溴和碘的合成效率较高，在成本计算中，氯的成本较低。
本实施例中，所述R 1或所述R 2为碳原子数为1～22的烷基、碳原子数为1～22的烷氧基、碳原子数为1～22的杂烷基或碳原子数为6～60的芳香基团，所述Ar包括氕、氘、氚、碳原子数为6～60的芳香基团、碳原子数为6～60的芳胺基团、碳原子数为6～60的杂芳胺基团及碳原子数为10～60的稠环基团中的任意一种或多种的组合，所述有机化合物可能用于蒸镀材料，C为碳原子，C数越多，分子量越大，越不利于蒸镀，量产蒸镀分子要求分子量为小于1000。
本实施例中，所述Ar包括含氮的芳香基团或含氮的杂芳香基团，其中氮元素可以使所述有机化合物具有较强的给电子能力，提高所述有机化合物的迁移率性能。
本实施例中，所述Ar为含苯环的轴对称基团。含苯环的轴对称基团可以通过基团的轴对称性，加强所述有机化合物的稳定性。
本实施例中，所述芳香基团包括含氧芳香基团或含硅芳香基团，所述芳胺基团包括含氧芳胺基团或含硅芳胺基团，所述稠环基团包括萘、蒽、芘中的任意一种。硅元素或氧元素的加入，可以提高所述有机化合物的给电子能力，提高所述有机化合物的迁移率性能。
本实施例中，所述R 1或所述R 2分别独立的为甲基、乙基或苯基中的任一种。所述有机化合物可能用于蒸镀材料，甲基、乙基或苯基的分子量较低，有利于蒸镀，且合成简单。
本实施例中，所述Ar为以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000036
Figure PCTCN2021095380-appb-000037
本实施例中，所述Ar通过不同分子量的基团来调节所述有机化合物的迁移率性能，通过对称性的基团提升所述有机物的稳定性；通过含氮、氧的基团，提升所述有机物的迁移率性能，并且可以有效调节分子量，同时，氮氧可以形成分子间与分子内氢键，进一步提高所述有机物的稳定性。
本实施例中，所述有机化合物的结构式为：
Figure PCTCN2021095380-appb-000038
其中，所述Ar为碳原子数为6～60的芳香基团或碳原子数为6～60的杂芳香基团。可以看出，所述R 1及所述R 2均为甲基，甲基是分子量低，进一步有利于蒸镀，降低合成难度，将主要设计方向集中于所述Ar，提高所述有机化合物的迁移率性能。
本实施例中，所述第一物质的结构式为：
Figure PCTCN2021095380-appb-000039
所述第二物质包括以下任意一种或多种的组合的基团：
Figure PCTCN2021095380-appb-000040
本实施例中，步骤S100位于惰性气体环境反应，所述惰性气体环境可以 为氩气、氦气中，可以保护所述有机化合物的稳定以及合成的效率。
本实施例中，步骤S100包括：
S110、将第一物质与第二物质混合按照摩尔比1:1～1:1.3的比例混合，以形成第一混合物。
本实施例中，步骤S110为将第一物质与第二物质混合按照摩尔比1:1.2的比例混合，以形成第一混合物。适当将所述第二物质的比例提高，可以提高所述第一物质的利用率，当所述第一物质与所述第二物质混合按照摩尔比1:1.2的比例混合时，既可以使反应充分，又可以避免所述第二物质过多浪费或使产物杂质过多而导致产品纯度不达标。
S120、将催化剂加入所述第一混合物中。
本实施例中，所述催化剂可以加快步骤S100，以提高所述有机化合物的制作效率。
本实施例中，所述催化剂可以为醋酸钯，醋酸钯既可以加快反应进行，又不会破坏所述有机化合物的性能，后期也较容易分离醋酸钯，方便快捷，加快了反应生产效能。
本实施例中，所述催化剂的物质的量与所述第一物质的物质的量比值为1:20～1:30。
本实施例中，所述催化剂的物质的量与所述第一物质的物质的量比值为1:25，此含量既可以保证催化效率，又可以在后期提纯分离催化剂时，方便分离，提高生产效率。
S130、将配体加入所述第一混合物中。
本实施例中，所述配体可以用于保护其他的官能团或是稳定一些容易反应的化合物，例如所述第二物质的芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种基团，以及所述第一物质中的所述R 1或所述R 2，以及所述第一物质中的氮杂环。
本实施例中，所述配体可以为三叔丁基膦四氟硼酸盐，用三叔丁基膦四氟硼酸盐作为配体，反应条件也不需要加入贵重的银盐，可以节省步骤加快合成复杂的多芳环化合物，使反应更加绿色环保，原子利用率高，体现了现在倡导的绿色化学的观念，此外对于官能团兼容性和反应效率也有一定帮助。
本实施例中，所述配体的物质的量与所述第二物质的物质的量的比值为1:8～1:12。
本实施例中，所述配体的物质的量与所述第二物质的物质的量的比值为1：10，此含量既可以保证保护所述第二物质的基团不会被破坏，又可以避免所述配体含量过多导致抑制反应的进行，保证了反应生产的效率。
S140、将碱加入所述第一混合物中。
本实施例中，所述碱用于提供碱性环境。所述碱可以为NaOt-Bu，NaOt-Bu不仅可以提供碱性环境，还有一定的催化效果，加快所述有机化合物的制作效率。
本实施例中，所述碱的物质的量与所述第二物质的物质的量的比值为1:0.8～1:1.2。
本实施例中，所述碱的物质的量与所述第二物质的物质的量的比值为1：1，此含量既可以保证碱性环境存在，又可以提高一定的反应速率，保证了反应生产的效率，同时又不会因为碱环境过高，使得所述有机化合物过于黏稠，不方便后续步骤的操作。
S150、将除水除氧的甲苯加入所述第一混合物中。
本实施例中，步骤S110～步骤S150可以同时进行。
本实施例中，步骤S110～步骤S150后，形成第二混合物。
S160、将所述第二混合物在120℃反应24小时，以形成第三混合物。
S170、将所述第三混合物冷却至室温。
S180、将所述第三混合物置于冰水中萃取并合并有机相，以形成第四混合物。
本实施例中，所述步骤S180的萃取剂可以为二氯甲烷。
S190、将所述第四混合物经旋蒸、柱层析分离纯化，以制备所述有机化合物。
本实施例中，柱层析的柱层析剂可以用体积比为1:1～1:10的二氯甲烷：正己烷。
本实施例中，柱层析的柱层析剂可以用体积比为1:5的二氯甲烷：正己烷.既可以达到良好的分离效果，又不会产生过多的浪费，节约生产成本。
本实施例中，所述有机化合物的结构包括以下任意一种或多种的组合：
Figure PCTCN2021095380-appb-000041
Figure PCTCN2021095380-appb-000042
Figure PCTCN2021095380-appb-000043
以
Figure PCTCN2021095380-appb-000044
Figure PCTCN2021095380-appb-000045
为例，三种化合物分别命名为化合物1、化合物2以及化合物3。
本实施例中，化合物1的HOMO电化学能级为-5.58eV，LUMO电化学能级为-2.43eV。化合物2的HOMO电化学能级为-5.61eV，LUMO电化学能级为-2.45eV。化合物3的HOMO电化学能级为-5.66eV，LUMO电化学能级为-2.44eV。可以看出，以三种结构为例，所述有机化合物的表征参数可以用于传输材料。
本实施例中，化合物1的反应式如下：
Figure PCTCN2021095380-appb-000046
本实施例中，化合物1的制作方法的步骤举例可以为向250mL二口瓶中加入原料1(2.92g，5mmol)，咔唑(1.00g，6mmol)，醋酸钯(45mg，0.2mmol)和三叔丁基膦四氟硼酸盐(0.17g，0.6mmol)，然后在手套箱中加入NaOt-Buu(0.58g，6mmol)，在氩气氛围下打入100mL事先除水除氧 的甲苯，在120℃反应24小时。冷却至室温，将反应液倒入200mL冰水中，二氯甲烷萃取三次，合并有机相，旋成硅胶，柱层析(二氯甲烷:正己烷，v:v为1:5)分离纯化，得白色粉末2.3g，MS(EI)m/z:[M] +:671.32，产率69％。
本实施例中，化合物2的反应式如下：
Figure PCTCN2021095380-appb-000047
本实施例中，化合物2的制作方法的步骤举例可以为向250mL二口瓶中加入原料1(2.92g，5mmol)，吩噁嗪(1.10g，6mmol)，醋酸钯(45mg，0.2mmol)和三叔丁基膦四氟硼酸盐(0.17g，0.6mmol)，然后在手套箱中加入NaOt-Buu(0.58g，6mmol)，在氩气氛围下打入100mL事先除水除氧的甲苯，在120℃反应24小时。冷却至室温，将反应液倒入200mL冰水中，二氯甲烷萃取三次，合并有机相，旋成硅胶，柱层析(二氯甲烷:正己烷，v:v，1:5)分离纯化，得白色粉末2.5g，MS(EI)m/z:[M] +:687.30，产率73％。
本实施例中，化合物3的反应式如下：
Figure PCTCN2021095380-appb-000048
本实施例中，化合物3的制作方法的步骤举例可以为向250mL二口瓶中加入原料1(2.92g，5mmol)，9,9’-二甲基吖啶(1.26g，6mmol)，醋酸钯(45mg，0.2mmol)和三叔丁基膦四氟硼酸盐(0.17g，0.6mmol)，然后在手套箱中加入NaOt-Buu(0.58g，6mmol)，在氩气氛围下打入100mL事先除水除氧的甲苯，在120℃反应24小时。冷却至室温，将反应液倒入200mL冰水中，二氯甲烷萃取三次，合并有机相，旋成硅胶，柱层析(二氯甲烷:正己烷，v:v，1:5)分离纯化，得白色粉末2.4g，MS(EI)m/z:[M] +:713.21，产率67％。
本发明实施例通过在吩嗪连芴的结构基础上，与其他基团配合，得到具有 高迁移率的有机化合物，增强了显示设备的显示效能。
本发明实施例还提供了一种显示面板100，包括发光器件层500，所述发光器件层500包括如任一上述的有机化合物或根据如任一上述的有机化合物的制作方法制作的所述有机化合物。
本发明实施例通过在吩嗪连芴的结构基础上，与其他基团配合，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
现结合具体实施例对本发明的技术方案进行描述。
所述显示面板100包括衬底200、位于所述衬底200上的阵列基板300、位于所述阵列基板300上的发光器件层500，所述发光器件层500包括如任一上述的有机化合物或根据如任一上述的有机化合物的制作方法制作的所述有机化合物，具体请参阅图1。
本实施例中，所述有机化合物的结构请参阅任一上述的有机化合物的实施例及任一上述的有机化合物的制作方法的实施例，在此不再赘述。
本实施例中，所述阵列基板300包括有源层、位于所述有源层上的第一绝缘层、位于所述第一绝缘层上的栅极层、位于所述栅极层上的第二绝缘层、位于所述第二绝缘层上的源漏极层以及位于所述源漏极层上的第三绝缘层。
本实施例中，所述显示面板100还包括靠近所述阵列基板300一侧的阳极层410、位于所述阳极层410上的发光器件层500、位于所述发光器件层500上的阴极层420以及位于所述阴极层420上的光耦合输出层430，具体请参阅图1。
本实施例中，发光器件层500包括位于所述阳极层410上的空穴注入层510、位于所述空穴注入层510上的空穴传输层520、位于所述空穴传输层520上的电子阻挡层530、位于所述电子阻挡层530上的发光材料层540、位于所述发光材料层540上的空穴阻挡层550、位于所述空穴阻挡层550上的电子传输层560以及位于所述电子传输层560上的电子注入层570，具体请参阅图1。
本实施例中，所述发光材料层540中的材料可以OLED或QLED(Quantum Dot Light Emitting Diodes，量子点发光二极管)，在此不做限制。
本实施例中，所述阳极层410包括第一ITO(氧化铟锡)层、位于所述第 一ITO层上的银层、位于所述银层上的第二ITO层，所述阳极层410为全反射的电极，可以提高所述发光器件层500的出光效率。
本实施例中，所述阴极层420为透明电极材料或半透明电极材料，可以包括ITO，增加所述发光器件层500的出光效率。
本实施例中，所述光耦合输出层430用于提高所述发光器件层500的出光效率，增强显示效果。
本实施例中，所述空穴传输层520包括所述有机化合物。所述有机化合物与所述空穴传输层520相配合，空穴传输效率可以得到最好的提升。
以
Figure PCTCN2021095380-appb-000049
Figure PCTCN2021095380-appb-000050
为例，三种化合物分别命名为化合物1、化合物2以及化合物3。
本实施例中，化合物1的HOMO电化学能级为-5.58eV，LUMO电化学能级为-2.43eV。化合物2的HOMO电化学能级为-5.61eV，LUMO电化学能级为-2.45eV。化合物3的HOMO电化学能级为-5.66eV，LUMO电化学能级为-2.44eV。可以看出，以三种结构为例，所述有机化合物的表征参数可以用于传输材料。
本实施例中，将化合物1、化合物2以及化合物3用于所述空穴传输层520。
本实施例中，包括所述化合物1的所述空穴传输层520的所述显示面板100的最高电流效率为40.1cd/A，对于红光色坐标(CIEx,CIEy)为(0.685,0.291)，最大外量子效率为36.7％。
本实施例中，包括所述化合物2的所述空穴传输层520的所述显示面板100的最高电流效率为36.8cd/A，对于红光色坐标(CIEx,CIEy)为 (0.684,0.290)，最大外量子效率为34.3％。
本实施例中，包括所述化合物3的所述空穴传输层520的所述显示面板100的最高电流效率为39.8cd/A，对于红光色坐标(CIEx,CIEy)为(0.686,0.292)，最大外量子效率为35.5％。
本实施例中，可以从上述表征数据看出，以化合物1、化合物2、化合物3为例的本发明实施例的所述有机化合物，可以作为空穴传输层520使用，具有高的电流效率，和较高的最大外量子效率，同时对于红光的发光色准也校准，本发明实施例的所述有机化合物可以作为发光器件层500的材料，特别是作为空穴传输层520的材料，有较好的工作效能，延长了所述显示面板100的使用寿命。
本发明实施例通过在吩嗪连芴的结构基础上，配上其他给电子基团，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
本发明实施例还提供了一种显示装置10，包括如任一上述的显示面板100。
所述显示面板100的具体结构请参阅任一上述显示面板100的实施例以及图1、图2，在此不再赘述。
本实施例中，所述显示装置10还包括位于所述显示面板100上的封装层20及盖板层30，具体请参阅图2。
本发明实施例通过在吩嗪连芴的结构基础上，配上其他给电子基团，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
本发明实施例公开了一种有机化合物及其制作方法、显示面板。该有机化合物如下述通式表示：
Figure PCTCN2021095380-appb-000051
其中，该Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，该R 1或该R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。本发明实施例通过在吩嗪连芴的结构基础上，与其 他基团配合，得到具有高迁移率的有机化合物，增强了显示设备的显示效能。
可以理解的是，对本领域普通技术人员来说，可以根据本申请的技术方案及其发明构思加以等同替换或改变，而所有这些改变或替换都应属于本申请所附的权利要求的保护范围。

Claims (20)

  1. 一种有机化合物，其中，所述有机化合物如下述通式表示：
    Figure PCTCN2021095380-appb-100001
    其中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。
  2. 根据权利要求1所述的有机化合物，其中，所述Ar包括氕、氘、氚、碳原子数为6～60的芳香基团、碳原子数为6～60的芳胺基团、碳原子数为6～60的杂芳胺基团及碳原子数为10～60的稠环基团中的任意一种或多种的组合，所述R 1或所述R 2为碳原子数为1～22的烷基、碳原子数为1～22的烷氧基、碳原子数为1～22的杂烷基及碳原子数为6～60的芳香基团中的任意一种或多种的组合。
  3. 根据权利要求2所述的有机化合物，其中，所述Ar为含苯环的轴对称基团。
  4. 根据权利要求3所述的有机化合物，其中，所述Ar为以下任意一种或多种的组合：
    Figure PCTCN2021095380-appb-100002
    Figure PCTCN2021095380-appb-100003
  5. 根据权利要求2所述的有机化合物，其中，所述芳香基团包括含氧芳香基团或含硅芳香基团，所述芳胺基团包括含氧芳胺基团或含硅芳胺基团，所述稠环基团包括萘、蒽、芘中的任意一种。
  6. 根据权利要求5所述的有机化合物，其中，所述Ar为以下任意一种或多种的组合：
    Figure PCTCN2021095380-appb-100004
    Figure PCTCN2021095380-appb-100005
  7. 根据权利要求1所述的有机化合物，其中，所述R 1或所述R 2分别独立的为甲基、乙基或苯基中的任一种。
  8. 根据权利要求1所述的有机化合物，其中，所述有机化合物的结构式为：
    Figure PCTCN2021095380-appb-100006
    其中，所述Ar为碳原子数为6～60的芳香基团或碳原子数为6～60的杂芳香基团。
  9. 根据权利要求1所述的有机化合物，其中，所述有机化合物的结构包括以下任意一种或多种的组合：
    Figure PCTCN2021095380-appb-100007
    Figure PCTCN2021095380-appb-100008
    Figure PCTCN2021095380-appb-100009
  10. 一种有机化合物的制作方法，其中，包括：
    将第一物质与第二物质混合，形成所述有机化合物，所述有机化合物由通式(1)表示：
    Figure PCTCN2021095380-appb-100010
    所述第一物质由通式(2)表示：
    Figure PCTCN2021095380-appb-100011
    其中，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合，所述X为卤素，所述第二物质包括芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种基团的组合，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺基团及稠环基团中的任意一种或多种的组合。
  11. 根据权利要求10所述的有机化合物的制作方法，其中，所述第一物质与所述第二物质的摩尔比为1:1至1:3。
  12. 一种显示面板，其中，包括发光器件层，所述发光器件层有机化合物，所述有机化合物如下述通式表示：
    Figure PCTCN2021095380-appb-100012
    其中，所述Ar包括氢及所述氢的同位素、芳香基团、芳胺基团、杂芳胺 基团及稠环基团中的任意一种或多种的组合，所述R 1或所述R 2分别独立的为烷基、烷氧基、杂烷基及芳香基团中的任意一种或多种的组合。
  13. 根据权利要求12所述的显示面板，其中，所述Ar包括氕、氘、氚、碳原子数为6～60的芳香基团、碳原子数为6～60的芳胺基团、碳原子数为6～60的杂芳胺基团及碳原子数为10～60的稠环基团中的任意一种或多种的组合，所述R 1或所述R 2为碳原子数为1～22的烷基、碳原子数为1～22的烷氧基、碳原子数为1～22的杂烷基及碳原子数为6～60的芳香基团中的任意一种或多种的组合。
  14. 根据权利要求13所述的显示面板，其中，所述Ar为含苯环的轴对称基团。
  15. 根据权利要求14所述的显示面板，其中，所述Ar为以下任意一种或多种的组合：
    Figure PCTCN2021095380-appb-100013
    Figure PCTCN2021095380-appb-100014
  16. 根据权利要求13所述的显示面板，其中，所述芳香基团包括含氧芳香基团或含硅芳香基团，所述芳胺基团包括含氧芳胺基团或含硅芳胺基团，所述稠环基团包括萘、蒽、芘中的任意一种。
  17. 根据权利要求16所述的显示面板，其中，所述Ar为以下任意一种或多种的组合：
    Figure PCTCN2021095380-appb-100015
    Figure PCTCN2021095380-appb-100016
  18. 根据权利要求12所述的显示面板，其中，所述R 1或所述R 2分别独立的为甲基、乙基或苯基中的任一种。
  19. 根据权利要求12所述的显示面板，其中，所述有机化合物的结构式为：
    Figure PCTCN2021095380-appb-100017
    其中，所述Ar为碳原子数为6～60的芳香基团或碳原子数为6～60的杂芳香基团。
  20. 根据权利要求12所述的显示面板，其中，所述有机化合物的结构包括以下任意一种或多种的组合：
    Figure PCTCN2021095380-appb-100018
    Figure PCTCN2021095380-appb-100019
    Figure PCTCN2021095380-appb-100020
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Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140042412A1 (en) * 2011-04-15 2014-02-13 Dong-wan Ryu Compound for organic optoelectronic device, organic light-emitting diode including the same and display device including the organic light-emitting diode
JP2014037353A (ja) * 2012-08-10 2014-02-27 Tosoh Corp 特定構造を有するジヒドロフェナジン化合物及びその用途
CN108203417A (zh) * 2016-12-20 2018-06-26 江苏三月光电科技有限公司 以芴为主体的有机化合物及有机电致发光器件
CN109761822A (zh) * 2019-01-23 2019-05-17 苏州久显新材料有限公司 芴类衍生物和电子器件
CN110299460A (zh) * 2019-06-24 2019-10-01 武汉华星光电半导体显示技术有限公司 一种空穴传输材料、制备方法及电致发光器件
CN110407817A (zh) * 2019-07-04 2019-11-05 武汉华星光电半导体显示技术有限公司 空穴传输材料及其制备方法、电致发光器件
CN110885317A (zh) * 2019-11-22 2020-03-17 武汉华星光电半导体显示技术有限公司 以二氢吩嗪为核的空穴传输材料及有机发光二极管
CN111056959A (zh) * 2019-11-04 2020-04-24 苏州久显新材料有限公司 芴类衍生物和电子器件
CN111205272A (zh) * 2020-02-20 2020-05-29 长春海谱润斯科技有限公司 一种有机电致发光器件用材料及其有机电致发光器件
CN111635391A (zh) * 2020-07-06 2020-09-08 苏州久显新材料有限公司 芴类化合物和电子器件
CN112375002A (zh) * 2021-01-18 2021-02-19 苏州久显新材料有限公司 2,4,7-三取代芴类化合物及其电子器件

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140042412A1 (en) * 2011-04-15 2014-02-13 Dong-wan Ryu Compound for organic optoelectronic device, organic light-emitting diode including the same and display device including the organic light-emitting diode
JP2014037353A (ja) * 2012-08-10 2014-02-27 Tosoh Corp 特定構造を有するジヒドロフェナジン化合物及びその用途
CN108203417A (zh) * 2016-12-20 2018-06-26 江苏三月光电科技有限公司 以芴为主体的有机化合物及有机电致发光器件
CN109761822A (zh) * 2019-01-23 2019-05-17 苏州久显新材料有限公司 芴类衍生物和电子器件
CN110299460A (zh) * 2019-06-24 2019-10-01 武汉华星光电半导体显示技术有限公司 一种空穴传输材料、制备方法及电致发光器件
CN110407817A (zh) * 2019-07-04 2019-11-05 武汉华星光电半导体显示技术有限公司 空穴传输材料及其制备方法、电致发光器件
CN111056959A (zh) * 2019-11-04 2020-04-24 苏州久显新材料有限公司 芴类衍生物和电子器件
CN110885317A (zh) * 2019-11-22 2020-03-17 武汉华星光电半导体显示技术有限公司 以二氢吩嗪为核的空穴传输材料及有机发光二极管
CN111205272A (zh) * 2020-02-20 2020-05-29 长春海谱润斯科技有限公司 一种有机电致发光器件用材料及其有机电致发光器件
CN111635391A (zh) * 2020-07-06 2020-09-08 苏州久显新材料有限公司 芴类化合物和电子器件
CN112375002A (zh) * 2021-01-18 2021-02-19 苏州久显新材料有限公司 2,4,7-三取代芴类化合物及其电子器件

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