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Organic electroluminescent compound of phenazine derivative

A technology of derivatives and compounds, applied in the field of organic electroluminescence, which can solve problems such as low electron mobility, low electron mobility, and voltage drop

Active Publication Date: 2015-05-27
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, when the OLED device is operated with an applied voltage, it will generate Joule heat, which makes the organic material easy to crystallize, which affects the life and efficiency of the device. Therefore, it is also necessary to develop stable and efficient organic electroluminescent materials.
[0005] In OLED materials, since most organic electroluminescent materials transport holes faster than electrons, it is easy to cause an imbalance in the number of electrons and holes in the light-emitting layer, so that the efficiency of the device is relatively low.
Tris(8-hydroxyquinoline)aluminum (Alq 3 ) has been widely studied since its invention, but as an electron transport material, its electron mobility is still very low, and it will degrade itself. In the device using it as an electron transport layer, there will be a voltage drop , at the same time, due to the lower electron mobility, a large number of holes enter the Alq 3 In the layer, the excess holes radiate energy in a non-luminescent form, and when used as an electron-transporting material, its application is limited due to its green-emitting properties.

Method used

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  • Organic electroluminescent compound of phenazine derivative
  • Organic electroluminescent compound of phenazine derivative
  • Organic electroluminescent compound of phenazine derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0074] Synthesis of compound 1

[0075]

[0076] Synthesis of Intermediate 1-1

[0077] In a dry 100ml single-necked bottle, add phenanthrenequinone (2g, 9.6mmol), 4-bromo-o-phenylenediamine (1.8g, 9.6mmol), 50ml of absolute ethanol, and 25ml of acetic acid in sequence. After stirring at room temperature for 0.5 h, it was filtered to obtain 2.3 g of light yellow solid with a yield of 67%. 1 H NMR (400MHz, CDCl 3 )δ: 9.36(d, J=7.9Hz, 2H), 8.57(d, J=8.0Hz, 2H), 8.52(d, J=2.1Hz, 1H), 8.19(d, J=9.0Hz, 1H) ,7.91(dd,J=9.0,2.1Hz,1H),7.82(t,J=7.5Hz,2H),7.75(t,J=7.5Hz,2H).

[0078] Synthesis of compound 1

[0079] In a dry 50ml single-necked bottle, sequentially add intermediate 1-1 (0.3g, 8.4mmol), 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronic acid (0.27g, 8.4mmol) , K 2 CO 3 (2.3g, 16.8mmol), THF (30ml), water (5ml) and tetrakistriphenylphosphine palladium (50mg, 0.05mmol), under the protection of argon, the reaction solution was heated to reflux and stirred for 3h. After...

Embodiment 2

[0081] Synthesis of compound 17

[0082]

[0083] Synthesis of Intermediate 17-1

[0084] The synthesis method was similar to the synthesis of intermediate 1-1, and finally a light green solid was obtained with a yield of 60%. 1 H NMR (400MHz, CDCl 3 )δ: 9.59 (ddd, J = 8.1, 5.0, 1.8Hz, 2H), 9.29 (dd, J = 4.4, 1.7Hz, 2H), 8.55 (d, J = 2.1Hz, 1H), 8.21 (d, J =9.0Hz,1H),7.98(dd,J=9.0,2.2Hz,1H),7.80(ddd,J=8.1,4.5,1.4Hz,2H).

[0085] Synthesis of compound 17

[0086] In a dry 50ml single-necked bottle, sequentially add intermediate 17-1 (0.3g, 0.84mmol), 4-(1-phenyl-1H-benzimidazol-2-yl)phenylboronic acid (0.27g, 0.84mmol) , K 2 CO 3 (2.3g, 16.8mmol), THF (30ml), water (5ml) and tetrakistriphenylphosphine palladium (50mg, 0.05mmol), under the protection of argon, the reaction solution was heated to reflux and stirred for 3h. After the reaction stopped, Return to room temperature, wash with water, extract with dichloromethane, combine the organic phases, spin dry, and sepa...

Embodiment 3

[0088] Synthesis of compound 47

[0089]

[0090] Synthesis of Intermediate 47-1

[0091]Add compound 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (2g, 5.1mmol), biboronic acid pinacol ester (1.5g, 6.18mmol) in the flask ), potassium acetate (15.4mmol), Pd(dppf) 2 Cl 2 (100mg), 40ml of N,N-dimethylformamide, heated to 90°C for 12 hours under nitrogen protection, cooled, poured into water, extracted with dichloromethane, dried with anhydrous sodium sulfate, concentrated, the crude product was used Silica gel column purification afforded 1.5 g of white solid with a yield of 68%. 1 H NMR (400MHz, CDCl 3, δ): 8.75-8.80 (m, 6H), 8.00-8.02 (d, J=8Hz, 2H), 7.57-7.63 (m, 6H), 1.40 (s, 12H).

[0092] Synthesis of compound 47

[0093] In a dry 50ml single-necked bottle, sequentially add intermediate 47-1 (0.4g, 0.92mmol), intermediate 1-1 (0.33g, 0.92mmol), K 2 CO 3 (2.3g, 16.8mmol), THF (30ml), water (5ml) and tetrakistriphenylphosphine palladium (50mg, 0.05mmol), under the...

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Abstract

The invention provides an organic electroluminescent compound of a phenazine derivative. The organic electroluminescent compound is a compound shown in a structural formula I. The organic electroluminescent compound can be used for preparing an organic electroluminescent apparatus. The formula is shown in the description.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to an organic electroluminescence compound of phenazine derivatives. Background technique [0002] Organic electroluminescent devices (OLEDs) are devices prepared by depositing a layer of organic materials between two metal electrodes by spin coating or vacuum evaporation. A classic three-layer organic electroluminescent device includes a hole transport layer, emissive layer and electron transport layer. The holes generated by the anode are combined with the electrons generated by the cathode through the hole transport layer to form excitons in the light emitting layer through the hole transport layer, and then emit light. Organic electroluminescent devices can be adjusted to emit various required lights by changing the material of the light-emitting layer as required. [0003] As a new type of display technology, organic electroluminescent devices have self-illumination...

Claims

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Application Information

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IPC IPC(8): C07D403/10C07D403/14C07D405/14C07D471/14C07D401/04C07D403/04C07D401/10C07D401/14C09K11/06H01L51/54
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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