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Organic blue light micromolecules based on anthracene-tetraphenylethylene and application of organic blue light micromulecules to preparation of non-doped organic electroluminescence device

An electroluminescent device, tetrastyrene technology, applied in the direction of electro-solid devices, electrical components, luminescent materials, etc., can solve the problems of low efficiency, device efficiency roll-off, etc., achieve simple synthesis, small efficiency roll-off, excellent electrical The effect of luminescence properties

Active Publication Date: 2019-04-12
JILIN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] For this reason, the object of the present invention is to provide a class of anthracene-tetraphenylethylene organic blue-light small molecule light-emitting materials with high solid-state luminous efficiency and high exciton utilization rate with asymmetric structure, which can be used as a non-doped Blue OLED devices can obtain high efficiency at high brightness, which overcomes the problems of low efficiency of traditional fluorescent materials and serious device efficiency roll-off of phosphorescent materials or TADF materials at high brightness

Method used

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  • Organic blue light micromolecules based on anthracene-tetraphenylethylene and application of organic blue light micromulecules to preparation of non-doped organic electroluminescence device
  • Organic blue light micromolecules based on anthracene-tetraphenylethylene and application of organic blue light micromulecules to preparation of non-doped organic electroluminescence device
  • Organic blue light micromolecules based on anthracene-tetraphenylethylene and application of organic blue light micromulecules to preparation of non-doped organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: In the preparation of Example P1, the steps are as follows:

[0031] Synthesis of M1: Dissolve diphenylmethane (5.05mL, 30mmol) in 50mL of tetrahydrofuran, stir in an ice-water bath at 0°C, and add 13mL of n-butyllithium (2.4M, 30mmol) dropwise, in an ice-water bath at 0°C Stir for 30min. Then slowly add the mixed solution dropwise to the tetrahydrofuran solution containing 4-bromobenzophenone (6.50g, 25mmol), stir at room temperature for 6h, add saturated NH 4 Cl solution. The crude product was extracted with dichloromethane, and the extract was concentrated by rotary evaporation to obtain a white crude alcohol product. Dry the obtained crude alcohol product and dissolve it in 100mL of toluene, add p-toluenesulfonic acid (1.30g, 6.76mmol), reflux at 80℃ for 6h, use 10% NaHCO 3 The toluene layer was washed with the solution, extracted and separated, and concentrated to obtain a crude product, which was separated and purified by column chromatography with cycloh...

Embodiment 2

[0039] Example 2: Preparation of Example P2, the steps are as follows:

[0040] Synthesis of M4: M4 was synthesized by a one-pot method. In a 250mL round bottom flask, 9,10-phenanthrenequinone (6.24g, 30mmol), 4-bromobenzaldehyde (5.52g, 30mmol), aniline (14.3ML, 150mmol), ammonium acetate (9.24g, 120mmol) was dissolved in 150mL glacial acetic acid, and refluxed at 120°C for 4 hours. The reaction solution was poured into 100 mL of ice water, and a large amount of solids precipitated out instantly. Suction filtration, separation and purification by column chromatography (petroleum ether: dichloromethane = 1:1) to obtain a white solid (11.86 g, yield: 89%). MALDI-TOF (m / z)(M + ]: The measured value is 448.75 and the theoretical value is 448.06.

[0041]

[0042] Synthesis of M5: Dissolve M4 (4.48g, 10mmol) in 80mL freshly distilled tetrahydrofuran and place it in a low temperature reactor at -78℃ for 10min, freeze and degas three times, then slowly drop 6.2mL n-butyllithium (2.40M,...

Embodiment 3

[0046] Embodiment 3: The preparation of this embodiment P3, the steps are as follows:

[0047] Synthesis of P3: In a 100mL round-bottom flask, mix 4-(9H-carbazol-9-yl)phenylboronic acid (0.86g, 3mmol), M3(1.76g, 3mmol), tetrakistriphenylphosphine palladium (80mg, 0.070mmol), potassium carbonate (5.52g, 40mmol) was dissolved in 40mL toluene and 20mL aqueous solution, and refluxed at 90°C for 24 hours under nitrogen protection. The liquid was extracted and separated with dichloromethane, concentrated to obtain a crude product, which was separated and purified by column chromatography (petroleum ether: dichloromethane=2:1) ​​to obtain a yellow solid (1.75 g, yield: 78%). 1 H NMR (500MHz, CD 2 Cl 2 , ppm, δ): 8.26(t,J=6.9Hz,2H),7.89(m,J=7.6,5.7Hz,4H),7.79–7.71(m,5H),7.58–7.53(m,2H), 7.51–7.43(m,4H),7.43–7.36(m,2H),7.34(d,J=8.1Hz, 2H),7.32–7.19(m,18H); mass spectrum MALDI-TOF(m / z)[M + ]: The measured value is 749.54 and the theoretical value is 749.96. Elemental analysis: C 58 H 39 T...

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Abstract

The invention discloses organic blue light micromolecule materials based on anthracene-tetraphenylethylene and application of organic blue light micromulecule materials to preparation of a non-doped organic electroluminescence device, and belongs to the technical field of organic photoelectric materials. An organic electroluminescence material is an anthracene-tetraphenylethylene derivative basedon asymmetry, anthracene groups having the feature of triplet state-triplet state annihilation (TTA) and tetraphenylethylene groups with high solid-state light-emitting efficiency are reasonably connected, the high solid-state light-emitting efficiency can be realized, and the utilization rate of excitons can be increased based on the TTA principle. The prepared non-doped blue light organic electroluminescence device with the organic blue light micromolecule materials being a light-emitting layer can obtain high efficiency under high brightness, and the problem is solved that the efficiency ofa traditional fluorescent material is low, and a device made from a phosphor material or thermal activation delay fluorescent material has severe roll-off of efficiency under high brightness.

Description

Technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and specifically relates to a class of anthracene-tetrastyrene-based organic blue light small molecule materials and their applications in preparing non-doped organic electroluminescent devices. Background technique [0002] Organic electroluminescent diodes (OLED) are considered to be the next generation display technology that can replace inorganic light-emitting diodes due to their flexibility, flexibility, wide viewing angle, and energy saving. High-efficiency red, green, and blue primary color materials are indispensable in full-color display. At present, both red and green light materials have reached commercial requirements, but high-efficiency blue light materials are still lacking, so high-performance blue light Organic materials are a key issue in the OLED field. [0003] At present, the most popular phosphorescent materials and thermally activated delayed fluorescence...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D235/02C07D209/86C07C211/55C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07C211/55C07D209/86C07D235/02C09K2211/1044C09K2211/1029C09K2211/1011C09K2211/1014C09K2211/1007H10K85/615H10K85/6572H10K50/11
Inventor 路萍刘福通刘辉
Owner JILIN UNIV
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