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Compound based on carbazole derivative

A technology of carbazole derivatives and compounds, applied in the field of organic electroluminescent materials, can solve problems such as lower device efficiency, difficult electron flow, and charge imbalance in the light-emitting layer

Active Publication Date: 2015-06-03
SHANGHIA TAOE CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the characteristics of CBP that holes are easy to transport and electrons are difficult to flow, the charge in the light-emitting layer is unbalanced, which reduces the efficiency of the device.

Method used

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  • Compound based on carbazole derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] The synthesis of embodiment 1 compound 18

[0066]

[0067] Synthesis of Intermediate 18-1

[0068] In the there-necked flask, add m-bromobenzaldehyde (5.5g), phenanthrenequinone (6g), aniline (4.5g), ammonium acetate (8g) and acetic acid (100ml), under nitrogen protection, reflux 12 hours, cool, add water, It was extracted with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and the crude product was recrystallized with ethanol and dichloromethane to obtain 8.5 g of the product with a yield of 65%. 1 H NMR (400MHz, CDCl 3 ):δ8.46-8.86(d, J=7.6Hz, 1H), 8.76-8.78(d, J=8.4Hz, 1H), 8.70-8.72(d, J=8.4Hz, 1H), 7.83(s, 1H),7.10-7.77(m,13H).

[0069] Synthesis of Intermediate 18-2

[0070] Add compound 18-1 (4.49g, 10mmol), diboronic acid pinacol ester (3.0g, 12mmol), potassium acetate (3.0g), dichloroditriphenylphosphine palladium (50mg), dioxygen Hexacyclic (60mL), heated to 100°C for 12h, passed through silica gel while hot, washed the filter cak...

Embodiment 2

[0079] The synthesis of embodiment 2 compound 19

[0080]

[0081] Synthesis of Intermediate 19-1

[0082] Add intermediate 18-4 (10g, 35.3mmol), m-bromoiodobenzene (12g, 42mmol), potassium tert-butoxide (7.9g, 70.6mmol), palladium acetate (0.3g, 1.3mmol), three Tert-butylphosphine tetrafluoroborate (0.8g, 2.7mmol) and toluene (150mL), heated to reflux for 24 hours under nitrogen protection, cooled, removed toluene, added dichloromethane, washed with water, dried, and the crude product was passed through the column to obtain 11 g of product, 71% yield. 1 H NMR (400MHz, CDCl 3 ):δ8.43(s,1H),8.18-8.20(d,J=7.6Hz,1H),7.85-7.87(d,J=7.6Hz,1H),7.83-7.88(m,1H),7.64- 7.66(m,1H),7.28-7.59(m,9H),1.52(s,6H).

[0083] Synthesis of Compound 19

[0084] Add intermediate 19-1 (2.1g, 4.8mmol), intermediate 18-2 (2.4g, 4.8mmol), potassium carbonate (3g), tetrakistriphenylphosphine palladium (30mg), tetrahydrofuran (20mL) in a single-necked flask ), water (11 mL), heated to 80 ° C for 2...

Embodiment 3

[0086] Fabrication of Organic Electroluminescent Devices

[0087] Preparation of OLED using compound 19 of Example 2

[0088] First, the transparent conductive ITO glass substrate 110 (with the anode 120 on it) (China CSG Group Co., Ltd.) is washed with deionized water, ethanol, acetone and deionized water in sequence, and then treated with oxygen plasma for 30 seconds.

[0089] Then, a 5nm thick HAT-CN is vapor-deposited on the ITO as the hole injection layer 130

[0090] Then, TAPC was evaporated to form a hole transport layer 140 with a thickness of 65 nm.

[0091] Then, a 10nm-thick light-emitting layer 150 was evaporated on the hole-transport layer, in which compound 19 was used as the host light-emitting material, and 7% by weight Ir(ppy)2acac was used as the phosphorescence-doped guest material.

[0092] Then, 50 nm thick TmPyPB was vapor-deposited on the light emitting layer as the electron transport layer 160 .

[0093] Finally, 1nm LiF was vapor-deposited as the e...

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PUM

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Abstract

The invention discloses a compound based on a carbazole derivative. The compound has a structural formula I shown in the specification. The compound based on the carbazole derivative can be used for manufacturing an organic electroluminescence device and has the characteristic of high stability.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a compound based on carbazole derivatives. technical background [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, wide viewing...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07D519/00C07D491/048C07D403/10C07D471/04C07D495/04C09K11/06H01L51/54
CPCC09K11/06C07D403/10C07D471/04C07D487/04C07D491/048C07D495/04C07D519/00C09K2211/1029C09K2211/1007C09K2211/1044C09K2211/1092C09K2211/1088H10K85/653H10K85/654H10K85/655H10K85/657H10K85/6572H10K50/00
Inventor 黄锦海苏建华
Owner SHANGHIA TAOE CHEM TECH CO LTD
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