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Spirofluorene triphenylamine derivatives and their applications in organic electroluminescent devices

An organic light-emitting layer and electroluminescence technology, applied in the fields of electric solid devices, organic chemistry, light-emitting materials, etc., can solve the problems of spectral impurity, low voltage, low blue light efficiency, etc., and achieve high carrier mobility and driving voltage. The effect of small, high triplet energy levels

Active Publication Date: 2021-11-16
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And it has been successfully applied in light-emitting devices. Compared with blue light devices, green light and red light have achieved high efficiency and high stability. Blue light has low efficiency, spectral impurity, and low voltage. obstacle

Method used

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  • Spirofluorene triphenylamine derivatives and their applications in organic electroluminescent devices
  • Spirofluorene triphenylamine derivatives and their applications in organic electroluminescent devices
  • Spirofluorene triphenylamine derivatives and their applications in organic electroluminescent devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] The compound shown in formula (1), its structural formula is as follows:

[0049]

[0050] The reaction scheme and concrete preparation method of the compound shown in formula (1) are as follows:

[0051]

[0052] (1) Under the protection of argon, 2-bromodibenzothiophene and 1-fluorenoneboronic acid (0.69 g, 2.4 mmol) were mixed in 60 mL of tetrahydrofuran (THF) solvent. Add catalyst Pd(PPh 3 ) 4 , to obtain a mixed solution. After heating the mixed solution at 50 °C for 10 min, a concentration of 2M K was added 2 CO 3 Aqueous solution 15mL. The reaction time is 12 hours, and the reaction temperature is 50 degrees Celsius. Wait for the temperature of the mixed liquid to drop to room temperature, remove THF under vacuum, add 100 mL of dichloromethane to the residual solid, then add 100 mL of water to wash, repeat 3 times, and finally remove water under vacuum. The obtained residue was purified by silica gel column, eluting with petroleum ether / dichlorometha...

Embodiment 2

[0064] Utilize the synthetic compound SPIRO-SO2-TPA of embodiment 1 to prepare electroluminescent device, its structure is as follows figure 2 As shown, a glass substrate 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, an organic light-emitting layer 6, a hole blocking layer 7, and an electron transport layer are sequentially arranged from bottom to top. 8. The electron injection layer 9 and the cathode layer 10 are composed. The preparation steps of the above electroluminescent device are as follows:

[0065] Step 1: After the patterned ITO conductive glass substrate 1 is repeatedly ultrasonicated three times in an ultrasonic machine with acetone and ethanol, it is baked in an oven at 100°C until dry and ready for use. ITO serves as the anode layer 2 .

[0066] Step 2: Place the ITO conductive glass substrate 1 in the vacuum chamber with ozone for 15 minutes, and evacuate to 4.0×10 -4 Pa or so.

[0067] Step 3: On th...

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Abstract

The present invention relates to a spirofluorenetriphenylamine derivative represented by formula (1). The invention also discloses the application of the compound represented by formula (1) in the preparation of organic electroluminescent devices or organic fluorescent materials. The compound represented by formula (1) has a simple synthetic route, high synthetic yield, wide band gap, high triplet energy level, high carrier mobility and high thermal stability. The compound can be used in the light-emitting layer or the host in the OLED device, and can also be used in any layer in the device's transmission layer. The organic fluorescent material of the present invention has high fluorescence quantum yield and exhibits deep blue and high-efficiency properties in organic electroluminescent devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials and devices, in particular to a spirofluorenetriphenylamine derivative and its application in organic electroluminescent devices. Background technique [0002] Organic electroluminescent devices (OLEDs) have received more and more attention because of their unique properties, such as fast response time, high efficiency, and flexibility. Recently, phosphorescent materials can achieve 100% internal quantum efficiency because the presence of heavy metals can break the orbital spin rule, that is, they can effectively use 25% of singlet and 75% of triplet excitons under electrical excitation, while traditional fluorescent materials 75% of the triplet excitons will not be available leading to inefficiency. Phosphorescent materials can realize high-efficiency devices, showing excellent performance in blue, green, and red devices. CN 102911145A discloses a dibenzoheterocyclic spirobif...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/04C09K11/06H01L51/54
CPCC07D409/04C09K11/06C09K2211/1029C09K2211/1092H10K85/6576H10K85/6572
Inventor 廖良生田起生阳生熠蒋佐权
Owner SUZHOU UNIV