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CN-117209523-B - Fluorene-containing arylamine compound and organic electroluminescent device thereof

CN117209523BCN 117209523 BCN117209523 BCN 117209523BCN-117209523-B

Abstract

The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound containing fluorene and an organic electroluminescent device thereof. The fluorene-containing aromatic amine compound provided by the invention has proper hole mobility, can effectively improve the charge transmission efficiency of a device, further improves the driving voltage and luminous efficiency of the device, has proper HOMO and T1 values, can be well matched with adjacent organic functional layers, can also block excitons from migrating to the interface of the luminous layer when adjacent to the luminous layer, avoid interface luminescence, and further avoid ageing of the device caused by heat generated by interface luminescence, and further improves the driving voltage, luminous efficiency and service life of the device.

Inventors

  • ZHOU WENTING
  • DU MINGZHU
  • LIU XIQING
  • HAN CHUNXUE

Assignees

  • 长春海谱润斯科技股份有限公司

Dates

Publication Date
20260505
Application Date
20230828

Claims (7)

  1. 1. An aromatic amine compound containing fluorene, which has a structure represented by formula (I): wherein Ar 1 is selected from one of the following structures: Wherein each occurrence of a 1 is selected from 1, 2, 3, or 4, each occurrence of b 1 is selected from 1, 2, or 3, each occurrence of c 1 is selected from 1 or 2, each occurrence of d 1 is selected from 1; r 11 、R 21 is independently selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tertiary butyl, phenyl, deuterated phenyl, phenyl substituted by fluorine atoms, phenyl substituted by cyano, phenyl substituted by methyl, phenyl substituted by tertiary butyl, naphthyl, anthryl, phenanthryl, biphenyl and pyridyl; R 31 is selected from one of methyl, deuterated methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, deuterated phenyl, fluorine atom-substituted phenyl, cyano-substituted phenyl, methyl-substituted phenyl, tert-butyl-substituted phenyl, trifluoromethyl-substituted phenyl, trimethylsilyl-substituted phenyl, naphthyl, deuterated naphthyl, biphenyl, deuterium-substituted biphenyl, fluorine atom-substituted biphenyl, cyano-substituted biphenyl, methyl-substituted biphenyl, tert-butyl-substituted biphenyl, trifluoromethyl-substituted biphenyl, trimethylsilyl-substituted biphenyl, pyridyl; R 41 is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, tertiary butyl group, deuterated tertiary butyl group, phenyl group, deuterated phenyl group, fluorine atom substituted phenyl group, cyano group substituted phenyl group, methyl group substituted phenyl group, tertiary butyl group substituted phenyl group, trifluoromethyl group substituted phenyl group, trimethylsilyl group substituted phenyl group, pyridyl group and pyrimidinyl group; R 41a is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, n-propyl group, isopropyl group, deuterated isopropyl group, n-butyl group, tert-butyl group, deuterated tert-butyl group, phenyl group, deuterated phenyl group, fluorine atom substituted phenyl group, cyano group substituted phenyl group, methyl group substituted phenyl group, tert-butyl group substituted phenyl group, trifluoromethyl group substituted phenyl group, trimethylsilyl group substituted phenyl group, pyridyl group, pyrimidinyl group, and group of formula (II) identically or differently at each occurrence; Ar 2 is selected from substituted or unsubstituted pyridyl or one of the structures shown in the following: Wherein each occurrence of said a 201 is identically or differently selected from 1, 2, 3, 4, or 5, each occurrence of said b 201 is identically or differently selected from 1, 2, 3, or 4, each occurrence of said c 201 is identically or differently selected from 1, 2, or 3, each occurrence of said d 201 is identically or differently selected from 1, 2, 3, 4, 5, or 6, each occurrence of said e 201 is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, or 8, each occurrence of said f 201 is identically or differently selected from 1 or 2, each occurrence of said g 201 is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10, each occurrence of said h 201 is identically or differently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 11, 13, or 13; R 201 is selected from hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, tertiary butyl group, deuterated tertiary butyl group, adamantyl group, norbornyl group, phenyl group which is substituted or unsubstituted by one or more than one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, tertiary butyl group, deuterated tertiary butyl group, adamantyl group and norbornyl group; R 202 is selected from phenyl which is substituted or unsubstituted by one or more than one of deuterium atom, fluorine atom, cyano group, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl and naphthyl, naphthyl which is substituted or unsubstituted by one or more than one of deuterium atom, fluorine atom, cyano group, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl, norbornyl and naphthyl, biphenyl which is substituted or unsubstituted by one or more than one of deuterium atom, fluorine atom, cyano group, methyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, adamantyl and norbornyl; R 203 is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group and tert-butyl group, which are the same or different at each occurrence; ar 3 is selected from one of the following structures: Wherein each occurrence of said a 301 is identically or differently selected from 1,2,3,4, or 5, each occurrence of said b 301 is identically or differently selected from 1,2,3, or 4, each occurrence of said c 301 is identically or differently selected from 1,2, or 3, each occurrence of said d 301 is identically or differently selected from 1,2,3,4, 5, or 6, each occurrence of said e 301 is identically or differently selected from 1,2,3,4, 5, 6, 7, or 8, each occurrence of said f 301 is identically or differently selected from 1 or 2; r 301 is selected from hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, tertiary butyl group, deuterated tertiary butyl group, adamantyl group, norbornyl group, phenyl group which is substituted or unsubstituted by one or more than one of deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, tertiary butyl group, deuterated tertiary butyl group, adamantyl group and norbornyl group; R 302 is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, isopropyl group and tert-butyl group, which are the same or different at each occurrence; L 1 ~L 3 is independently selected from a single bond or one of the structures shown below: Wherein each occurrence of said a 401 is selected from the group consisting of 0, 1,2, 3, and 4 identically or differently, each occurrence of said b 401 is selected from the group consisting of 0, 1,2, and 3 identically or differently, each occurrence of said c 401 is selected from the group consisting of 0, 1, and 2 identically or differently, each occurrence of said d 401 is selected from the group consisting of 0, 1,2, 3,4,5, and 6 identically or differently, each occurrence of said e 401 is selected from the group consisting of 0, 1,2, 3,4,5, 6, 7, and 8 identically or differently; R 401 is selected from hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group; R 402 is selected from one of hydrogen atom, deuterium atom, fluorine atom, cyano group, methyl group, deuterated methyl group, trifluoromethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group and deuterated tert-butyl group, which are the same or different at each occurrence; Provided that at least one of said Ar 1 、Ar 2 、Ar 3 contains at least one group of formula (II): Wherein Ar 101 is selected from one of single bond, substituted or unsubstituted phenylene, ar 102 ~Ar 104 is independently selected from one of substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C6-C14 aryl; "substituted or unsubstituted" in "substituted or unsubstituted pyridyl" in Ar 2 and "substituted or unsubstituted" in Ar 101 ~Ar 104 mean that it is not substituted or substituted with one or more substituents selected from the group consisting of deuterium atom, halogen atom, cyano group, C1-C12 alkyl group.
  2. 2. The fluorene-containing arylamine compound according to claim 1, wherein said Ar 1 is selected from one of the structures shown below: 。
  3. 3. The fluorene-containing arylamine compound according to claim 1, wherein said Ar 2 is selected from one of the structures shown below: 。
  4. 4. the fluorene-containing arylamine compound according to claim 1, wherein said Ar 3 is selected from one of the structures shown below: 。
  5. 5. the fluorene-containing arylamine compound according to claim 1, wherein said L 1 ~L 3 is independently selected from a single bond or one of the structures shown below: 。
  6. 6. the fluorene-containing aromatic amine compound is characterized in that the fluorene-containing aromatic amine compound is selected from one of the following compounds: 。
  7. 7. an organic electroluminescent device comprising an anode, a cathode and an organic layer, wherein the organic layer comprises at least one of a hole transport region, a light emitting layer, an electron transport region and a cover layer on a side of the cathode facing away from the anode between the anode and the cathode, and the organic layer comprises a hole transport region, a light emitting layer and an electron transport region, wherein the hole transport region contains one or more fluorene-containing aromatic amine compounds according to any one of claims 1 to 6.

Description

Fluorene-containing arylamine compound and organic electroluminescent device thereof Technical Field The invention relates to the technical field of organic photoelectric materials, in particular to an aromatic amine compound containing fluorene and an organic electroluminescent device thereof. Background An Organic Light-Emitting Diode (OLED) has the characteristics of Light and thin body, wide viewing angle, fast response speed, wide use temperature range, low energy consumption, high efficiency, good color purity, high definition, good flexibility, and the like, and has been widely used in the fields of illumination and display, and is considered as one of the display and illumination technologies with the most development prospects in the industry. The classical OLED device is in a sandwich structure, a luminescent layer is sandwiched between two electrodes of a cathode and an anode, wherein the luminescent layer contains luminescent substances (guest materials), a certain working voltage is applied between the two electrodes, so that holes and electrons are respectively injected from the anode and the cathode and then reach the luminescent layer, excitons are generated by recombination, energy is released, the excitons migrate under the action of an electric field, energy is transferred to the luminescent substances, electrons in molecules of the luminescent substances migrate from a ground state to an excited state, and the electrons migrate from the excited state to the ground state again due to unstable excited states, thereby releasing the energy in the form of light and generating a luminescence phenomenon. In general, the Lowest Unoccupied Molecular Orbital (LUMO) of the host material is higher than the guest material, and the Highest Occupied Molecular Orbital (HOMO) of the host material is lower than the guest material. In order to improve the performance of the device, more organic functional layers are arranged between the anode and the light-emitting layer and between the cathode and the light-emitting layer, and in general, a hole transmission region is arranged between the anode and the light-emitting layer and mainly plays a role in injecting and transmitting holes, including a hole injection layer, a hole transmission layer, a light-emitting auxiliary layer, an electron blocking layer and the like, and an electron transmission region is arranged between the cathode and the light-emitting layer and mainly plays a role in injecting and transmitting electrons, including an electron injection layer, an electron transmission layer, a hole blocking layer and the like. In addition to the organic functional layer between the anode and the cathode, a cover layer is provided on the outside of the light-emitting side electrode (away from the non-light-emitting side electrode). In general, the cover layer has a higher refractive index, and can improve the light transmittance of the device, change the light emission direction, and the like, thereby improving the light emission efficiency, color purity, and the like of the device. In order to further improve the performance of the OLED device, such as light emitting efficiency, color purity, driving voltage, and service life, it is necessary to develop a hole transport material that has high energy level matching with the light emitting layer and other adjacent organic functional layers, proper charge transport performance, and excellent stability. Disclosure of Invention In order to solve the technical problems, the invention provides an aromatic amine compound containing fluorene, which has proper hole mobility, proper HOMO and T1 values and good thermal stability and chemical stability, can be used as a hole transport material in an OLED device, can improve the performances of the OLED device such as luminous efficiency, service life and the like, and has a structure shown in a formula (I): Wherein Ar 1 is selected from one of the structures shown in the formula (I-A) or the formula (I-B): In the formula (I-A), R 1、R2 is independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C7 aliphatic ring and C6-C30 aromatic ring fused monovalent group, or R 1 and R 2 can be connected to form substituted or unsubstituted C5-C10 carbocycle, one of X 1～X8 is selected from C and L 1 in the formula (I), and one is selected from C and the formula (I-C) And the rest is independently selected from CR 4 or nitrogen atom, in the formula (I-B), Z is selected from one of oxygen atom, sulfur atom and NR 5、CR6R7, R 5 is selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C3-C7 aliphatic ring and C6-C30 aryl fused monovalent group, R 6、R7 is independently selected from one of substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted