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Series of deep blue metal iridium phosphorescence OLED materials

A C6-C60, I-1 technology, applied in the field of phosphorescent OLED materials, can solve the problem that blue metal iridium phosphorescent complexes cannot simultaneously satisfy high color purity luminous efficiency and the like

Inactive Publication Date: 2016-04-27
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The blue metal iridium phosphorescent complexes currently used in OLED display technology cannot meet the requirements of high color purity and high luminous efficiency at the same time. The development and application of new ligands is an effective way to solve this problem

Method used

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  • Series of deep blue metal iridium phosphorescence OLED materials
  • Series of deep blue metal iridium phosphorescence OLED materials
  • Series of deep blue metal iridium phosphorescence OLED materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] The preparation of embodiment 1 compound SLC-GIR16

[0071]

[0072] The first step: preparation of compound G-1

[0073]

[0074] 20g of 3,4,5-trifluorobenzamide and 200ml of DMF-DMA, heated to reflux and stirred for 10 hours, concentrated under reduced pressure to dryness, added 150ml of petroleum ether to the residue, stirred and dispersed, and suction filtered to obtain 25g Compound G-1, yellow solid, yield 96%.

[0075] The second step: the preparation of compound G-2

[0076]

[0077] Mix 20g of compound G-1 obtained in the previous step with 13g of 2,4,6-trimethylphenylhydrazine, add 100ml of 1,4-dioxane and 100ml of glacial acetic acid, and heat up to Stir the reaction at 90°C for 12 hours, cool to room temperature, pour the reaction solution into 500ml of ice water, extract the aqueous phase with ethyl acetate, dry the organic phase, filter, concentrate the filtrate to dryness under reduced pressure, and separate and purify the residue with a silica ...

Embodiment 2

[0089] The preparation of embodiment 2 compound SLC-GIR85

[0090]

[0091] 2.0g of SLC-GIR16 and 1.4g of compound G-2 prepared in Example 1 were dispersed with 50ml of glycerin, heated to 180°C under nitrogen protection, stirred for 8 hours, cooled to room temperature, and the reaction solution Poured into 200ml of 1N dilute hydrochloric acid, filtered with suction, washed the filter cake with water, separated and purified the obtained solid with a silica gel column to obtain 1.6g of SLC-GIR85, a yellow solid, with a yield of 64.8%.

[0092] Experimental data:

[0093] (1) 1 HNMR (δ, CDCl 3 ): 1.83(6H,s), 2.12(3H,s), 6.67~6.72(2H,m), 7.09~7.14(1H,m), 8.18(1H,s). LC-MS: 1142.4[M+1] confirms that the substance obtained by the reaction is indeed the compound SLC-GIR85;

[0094] (2) Glass transition temperature (DSC): \;

[0095] (3) UV maximum absorption wavelength (DCM): 295nm, 305nm;

[0096] (4) Phosphorescence emission wavelength (DCM): 470 nm.

Embodiment 3

[0097] The preparation of embodiment 3 compound SLC-GIR62

[0098]

[0099] The first step: preparation of compound G-1

[0100]

[0101]Referring to the synthesis method in the first step of Example 1, replace 3,4,5-trifluorobenzamide in Example 1 with 2,3,4,5-tetrafluorobenzamide to prepare G-1, a yellow solid , yield 86%.

[0102] The second step: the preparation of compound G-2

[0103]

[0104] Referring to the synthesis method in the second step of Example 1, the G-1 obtained in the previous step and 2,4,6-trimethylphenylhydrazine were condensed and ring-closed to obtain G-2, a yellow solid, with a yield of 76%.

[0105] The third step: preparation of compound G-3

[0106]

[0107] With reference to the synthetic method of the third step of Example 1, the G-2 and IrCl obtained in the previous step 3 ·3H 2 O undergoes a coordination reaction to obtain G-3, a yellow solid, with a yield of 82%.

[0108] Step 4: Preparation of Compound SLC-GIR62

[0109] ...

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Abstract

The invention discloses a series of deep blue metal iridium phosphorescence OLED materials. The structural general formulas of the above organic electrophosphorescence materials are represented by formula I-1 and formula I-2. The phosphorescence materials have high heat stability, high quantum efficiency and low doping proportion, and are a series of iridium complex electrophosphorescence materials containing 1,2,4-triazole rings. The above compounds have the characteristics of high luminescence efficiency, good heat stability, easily available raw materials, simple preparation, high total yield, great reduction of the cost of phosphorescence materials, and important application values.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display and relates to a series of dark blue metal iridium phosphorescent OLED materials. Background technique [0002] Organic electroluminescent diode (referred to as OLED) and related research As early as 1963, pope et al. first discovered the electroluminescence phenomenon of organic compound single crystal anthracene. In 1987, Kodak Corporation of the United States made an amorphous film device by evaporating organic small molecules, which reduced the driving voltage to less than 20V. This type of device is ultra-thin, fully cured, self-illuminating, high brightness, wide viewing angle, fast response speed, low driving voltage, low power consumption, bright color, high contrast, simple process, good temperature characteristics, and can realize flexible display. And other advantages, can be widely used in flat panel displays and surface light sources, so it has been widely...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/1092C09K2211/1088C09K2211/1059C09K2211/1029H10K85/342H10K50/17H10K50/11
Inventor 曹建华
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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