A kind of organic photoelectric material containing benzoheterocyclic structure and its preparation method and application

A technology of organic optoelectronic materials and heterocycles, applied in the fields of luminescent materials, organic chemistry, photovoltaic power generation, etc., can solve the problems of difficult carrier transport, carrier accumulation, and reduced device efficiency, and achieves improved fluorescence quantum efficiency, high Fluorescence quantum efficiency, the effect of enhancing luminous brightness

Active Publication Date: 2021-02-09
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The energy level difference of blue-light materials is generally relatively large. In order to avoid energy back-transmission, only host materials with higher energy levels than the light-emitting materials can be selected. Accumulation of flow electrons produces triplet-triplet exciton serious annihilation, that is, efficiency roll-off, which seriously affects the working life of the device
In addition, due to the wide bandgap of the blue light material itself, pure blue light / deep blue light materials usually have a lower HOMO and a higher LUMO energy level. The potential barrier of the carrier leads to the increase of the driving voltage, the difficulty of carrier transport, and the decrease of the balance; Pure (greater than 470nm), will also cause a reduction in device efficiency

Method used

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  • A kind of organic photoelectric material containing benzoheterocyclic structure and its preparation method and application
  • A kind of organic photoelectric material containing benzoheterocyclic structure and its preparation method and application
  • A kind of organic photoelectric material containing benzoheterocyclic structure and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: The above compound 1 of the present invention can be synthesized by the following method.

[0040]

[0041] In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 6-amino-1,4-benzodioxane (16.63g, 110mmol), 1-naphthaldehyde (17.18g, 110mmol), ammonium acetate (15.41g, 200mmol) was dissolved in 250g (based on the mass of phenanthrenequinone) and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours. The liquid phase monitoring showed that there was no remaining phenanthrenequinone, cooled to room temperature, and washed with ethanol Beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 40.20 g of the target compound with a yield of 84%. The quality is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z) = 478.5514, the theoretical molecular weight is 478.5510; Anal.Calcd for C 33 h 22 N 2 o 2 (%): C 82.83, H 4.63, N 5.85, Found: C 82.81, H 4.65, N 5.85.

Embodiment 2

[0042] Example 2: The above compound 22 of the present invention can be synthesized by the following method.

[0043]

[0044]In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 6-amino-1,4-benzodioxane (16.63g, 110mmol), 1-pyrenecarbaldehyde (25.55g, 110mmol), ammonium acetate (15.41g, 200mmol) was dissolved in 250g (based on the mass of phenanthrenequinone) and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours. The liquid phase monitoring showed that there was no remaining phenanthrenequinone, cooled to room temperature, and washed with ethanol Beat once with ethanol:ethyl acetate at a volume ratio of 10:1 to obtain 44.21 g of the target compound with a yield of 80%. The compound is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z)=552.6338, theoretical molecular weight is 552.6330; Anal.Calcd for C 39 h 24 N 2 o 2 (%): C 84.76, H 4.38, N 5.07, Found: C 84.75, H 4.40, N 5.06.

Embodiment 3

[0045] Example 3: The above compound 31 of the present invention can be synthesized by the following method.

[0046]

[0047] In a 500ml reaction flask, phenanthrenequinone (20.80g, 100mmol), 1,4-dimethyl-1,2,3,4-tetrahydroquinoxalin-6-amine (19.50g, 110mmol), 1- Anthracene formaldehyde (22.69g, 110mmol) and ammonium acetate (15.41g, 200mmol) were dissolved in 250g (based on the mass of phenanthrenequinone) of acetic acid and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 8 hours, and the liquid phase monitoring There was no remaining phenanthrenequinone, cooled to room temperature, and beating once with ethanol: ethyl acetate with a volume ratio of 10:1 to obtain 43.26 g of the target compound with a yield of 78%. The compound is characterized as follows: mass spectrometer MALDI-TOF-MS (m / z)=554.6968, theoretical molecular weight is 554.6970; Anal.Calcd for C 39 h 30 N 4 (%): C 84.45, H 5.45, N 10.10, Found: C 84.44, H 5.48, ...

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Abstract

The invention belongs to the technical field of photoelectric material application, and in particular relates to an organic photoelectric material containing a benzoheterocyclic structure and its application. This type of material is introduced into the carbon atom site of the five-membered aromatic heterocycle of phenanthroimidazole and the benzoaliphatic heterocycle at the nitrogen atom site at the same time. It is a kind of material that simultaneously satisfies the single triplet energy gap ΔE ST The material is smaller and the triplet energy level of the acceptor is twice higher than that of the singlet excited state. The electroluminescence mechanism of the coexistence system of RISC and TTA is to obtain high photoelectric conversion efficiency and solve the problems of efficiency roll-off and light color quality of current deep blue light materials. A feasible way is provided. Through the selection and structural design of the donor / acceptor, the organic photoelectric material containing the benzoheterocyclic structure provided by the present invention has excellent performance in organic electroluminescent devices independently as a light-emitting layer material or as a light-emitting layer doping material , the synthesis and purification process is simple, and can be applied to industrial production.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and in particular relates to an organic photoelectric material containing a benzoheterocyclic structure, a preparation method and application thereof. Background technique [0002] Organic electroluminescent device (OLED) is a new display technology with ultra-thin, high brightness, wide viewing angle, self-illumination, low power consumption, low cost, bendable and low temperature conditions (the liquid crystal in TFT-LCD is in It will solidify under such conditions) and can work normally. It is praised by the industry as the ideal and most promising next-generation display technology after LCD. [0003] As one of the three primary colors, blue light has been lagging behind the development of green and red OLEDs, and there are many problems that need to be solved, which is determined by the nature of blue OLED itself. Whether it is fluorescent or phosphorescent mater...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/00C07D403/04C07D411/04C07D409/04C07D413/04C07D417/04C07D401/04C07D421/04C09K11/06H01L51/50H01L51/54H01L51/42H01L51/46
CPCC07D405/00C07D403/04C07D411/04C07D409/04C07D413/04C07D417/04C07D401/04C07D421/04C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092C09K2211/1096H10K85/622H10K85/615H10K85/6576H10K85/6574H10K85/657H10K30/00H10K85/6572H10K50/00Y02E10/549
Inventor 穆广园庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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