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Aza-spirofluorene anthracene heterocyclic compound and application thereof in organic electroluminescence elements

A heterocyclic compound, azafluorene technology, applied in the field of organic electroluminescent functional materials, to achieve the effect of improving triplet energy, low voltage, and improving luminous stability

Active Publication Date: 2018-12-07
XIAN RUILIAN NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the fluorescent type uses singlet excitons to emit light, its internal quantum efficiency can only reach 25%.

Method used

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  • Aza-spirofluorene anthracene heterocyclic compound and application thereof in organic electroluminescence elements
  • Aza-spirofluorene anthracene heterocyclic compound and application thereof in organic electroluminescence elements
  • Aza-spirofluorene anthracene heterocyclic compound and application thereof in organic electroluminescence elements

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086]

[0087] Add 30g of compound 1, 12.6g of phenol, 300ml of dimethylformamide (DMF), 10ml of pyridine into a 500ml three-necked flask, and blow nitrogen for 15min, stir to dissolve the raw materials completely, add 26.4g of potassium carbonate, and 1.2g of cuprous iodide , stirred for 5 minutes, turned on and heated to 100°C, stirred and reacted for 8 hours, then took samples for monitoring, and cooled to room temperature after the raw materials were completely reacted. Add 2M hydrochloric acid solution to adjust the pH to acidic, a large amount of white solid precipitates, extract 3×500ml with ethyl acetate, combine the organic phases, wash with water until neutral, dry with anhydrous magnesium sulfate and spin dry the solvent, the obtained white solid is 32.8g dried in the air, The yield was 88.2%, and it was directly used in the next reaction without further treatment.

[0088] 1 H NMR (400MHz, CDC13) δ7.98 (d, J = 8.4, 1H), 7.36 (dd, J = 8.4, 1H), 7.30 (s, 1H), 7....

Embodiment 2

[0099]

[0100] Add 20g of compound 5 and 150ml of THF to a 500ml three-necked flask successively, blow in nitrogen gas, and cool to 0°C. 125ml of 1.0M in THF phenylmagnesium bromide solution was slowly added dropwise. After raising the temperature to room temperature and continuing the reaction for 2 h, sampling was carried out for detection. When the reaction of the raw materials was complete, the stirring was stopped, and aqueous ammonium chloride solution was added to quench the reaction. Static liquid separation, the aqueous phase was extracted once with dichloromethane, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and then purified by column to obtain 17.6 g of a yellow solid with a yield of 63.7%.

[0101] 1 H NMR (400MHz, CDC13) δ 9.13 (d, J = 8.4, 1H), 8.58 (d, J = 8.4, 1H), 8.04 (t, J = 8.4, 1H), 7.81 (d, J = 7.6, 2H), 7.54(t, J=7.6, 1H), 7.45(t, J=7.6, 2H);

[0102]

[0103] Add 16g compound 6, 20.3g...

Embodiment 3

[0112]

[0113] Add 8g compound 8, 8.2g diphenylamine, 6.7g potassium carbonate, 0.2g 1,10-phenanthroline, 100ml toluene in a 250ml three-necked flask, feed nitrogen, then add 0.2g cuprous bromide, and the reaction system is heated to The reaction was refluxed and stirred for 8 hours. After the complete reaction of the raw materials was monitored by TLC, it was cooled to room temperature, washed with water to neutrality, the organic phase was dried with anhydrous sodium sulfate for 2 hours and then filtered. After the concentrated solvent was passed through a silica gel column, toluene was recrystallized to obtain the target compound 3 as a white solid 9.5 g, yield 87.7%.

[0114] 1 H NMR (400MHz, CDC13) δ8.54 (d, J = 8.4, 1H), 7.87 (d, J = 7.6, 1H), 7.41 (d, J = 7.6, 1H), 7.14-7.16 (m, 3H) , 7.01(t, J=7.6, 8H), 6.89(t, J=8.4, 1H), 6.77(m, 2H), 6.62(t, J=7.6, 4H), 6.46(t, J=7.6, 8H ), 6.06(dd, J=7.6, 2H), 6.00(s, J=7.6, 2H);

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Abstract

The invention relates to an aza-spirofluorene anthracene heterocyclic compound and an application thereof in organic electroluminescence elements. The aza-spirofluorene anthracene heterocyclic compound is represented by a general formula (1) (shown in the description), wherein groups of furan, carbazole, thiophene, fluorine, heteraryl amino, acridine, phenazine and the like are linked to a matrixof the compound. According to the aza-spirofluorene anthracene heterocyclic compound, the transmission property of a current carrier can be improved, the triplet state energy of a material can be improved, the HOMO / LUMO value of the material can be optimized, the high brightness, low voltage, high efficiency and long service life of an organic EL element can be realized, meanwhile, the material prepared from the compound has relatively high heat stability, the luminescence stability of a light emitting device can be remarkably improved, and the compound can be widely used as a luminescent layer main body material for OLED light emitting devices and display devices.

Description

technical field [0001] The invention relates to the field of organic electroluminescent functional materials, in particular to an azafluorene spiroanthracene heterocyclic compound and its application in organic electroluminescent elements. Background technique [0002] As a self-luminous electronic component, organic electroluminescent OLED (Organic Light Emission Diodes) display lighting mechanism is a new photoelectric information technology that directly converts electrical energy into light energy with the help of organic semiconductor functional materials under the action of a DC electric field. kind of. Its luminous color can be a single red, green, blue, yellow light or a combination of white light. The biggest feature of OLED light-emitting display technology is ultra-thin, ultra-lightweight, surface-emitting and flexible display. It can be used to manufacture monochrome or full-color displays. As a new light source technology, it can also be used to make lighting p...

Claims

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Application Information

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IPC IPC(8): C07D491/107C07D495/10C07F5/02C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D491/107C07D495/10C07F5/02C09K2211/1007C09K2211/1029C09K2211/1037C09K2211/1033C09K2211/1092C09K2211/1088C09K2211/1096H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/11
Inventor 孙军刘凯鹏杨燕杨丹丹张宏科高仁孝
Owner XIAN RUILIAN NEW MATERIAL CO LTD
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