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
View PDF6 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

PropertyMeasurementUnit
thicknessaaaaaaaaaa
Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap