Pyrene derivative, luminescent device material and luminescent device

A technology for derivatives and optoelectronic devices, applied to pyrene derivatives, can solve problems such as lack of materials, and achieve the effects of easy availability of raw materials, reduction of vibration energy loss, and high-efficiency luminescence performance

Pending Publication Date: 2021-09-24
ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, host materials with both high triplet energy levels and good hole mobility are still lacking.

Method used

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  • Pyrene derivative, luminescent device material and luminescent device
  • Pyrene derivative, luminescent device material and luminescent device
  • Pyrene derivative, luminescent device material and luminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0091] Synthesis of compound 1

[0092]

[0093] Under an argon atmosphere, 39.4 g (100 mmol) of 1,8-dibromo-4-chloropyrene, 42.3 g (200 mmol) of dibenzo[b, d]furan-3-ylboronic acid, tetrakis(tri Phenylphosphine) palladium 1.16g (1.0mmol), 1.5M aqueous sodium carbonate solution 200ml (300mmol) and ethylene glycol dimethyl ether 800ml (DME), heated and stirred at 80°C overnight. Cool to room temperature, add 500ml of water, solid precipitates, filter, and the obtained solid is washed with ethanol to obtain 37.0g of 3,3'-(4-chloropyrene-1,8-diyl)dibenzo[b,d ] furan, yield 65%, HPLC purity 98.5%.

[0094] 1 HNMR(DMSO): δ8.52(d, 1H), 8.30(d, 1H), 8.15(d, 2H), 8.03~7.98(m, 4H), 7.82~7.76(m, 4H), 7.72~7.70( m,3H),7.54(m,2H),7.39~7.31(m,4H)

[0095]

[0096] Under an argon atmosphere, 56.9 grams (100 mmol) of 3,3'-(4-chloropyrene-1,8-diyl)dibenzo[b,d]furan, (3-phenylquinoxa Lin-2-yl)boronic acid 30.0g (120mmol), [1,3-bis(2,6-di-isopropylphenyl)-4,5-dihydroimidazol-2-yliden...

Embodiment 2

[0099] Synthesis of Compound 21

[0100]

[0101] Under argon atmosphere, 31.6g (100mmol) of 1-bromo-4-chloropyrene, 36.0g (100mmol) of 3-boronic acid-9,9'-spirobifluorene, tetrakis(triphenylphosphine) palladium 1.16g (1.0mmol), 200ml (300mmol) of 1.5M aqueous sodium carbonate solution and 800ml of ethylene glycol dimethyl ether (DME), heated and stirred at 80°C overnight. Cooled to room temperature, added 500ml of water, solid precipitated, filtered, and the obtained solid was washed with ethanol to obtain 38.6g of 3-(4-chloropyren-1-yl)-9,9'-spiro[fluorene]. Yield 70%, HPLC purity 98.9%.

[0102] 1 HNMR(DMSO): δ8.30(d, 1H), 8.18~8.15(m, 2H), 8.07~8.04(m, 2H), 7.92~7.89(m, 5H), 7.74~7.68(m, 4H), 7.55(d, 1H), 7.45(m, 2H), 7.38(m, 1H), 7.28~7.27(m, 5H)

[0103]

[0104] Under an argon atmosphere, 55.1 grams (100 mmol) of 3-(4-chloropyren-1-yl)-9,9'-spiro[fluorene], (3-phenylquinoxaline-2- Base) boronic acid 30.0g (120mmol), [1,3-bis(2,6-di-isopropylphenyl)-4,5-dihydr...

Embodiment 3

[0106] Synthesis of compound 27

[0107]

[0108] Under argon atmosphere, 39.4g (100mmol) of 1,8-dibromo-4-chloropyrene and 47.6g (200mmol) of (9,9-dimethyl-9H-fluoren-1-yl)boronic acid were added to the reactor 1.16g (1.0mmol) of tetrakis(triphenylphosphine)palladium, 200ml (300mmol) of 1.5M aqueous sodium carbonate solution and 1000ml of ethylene glycol dimethyl ether (DME), heated and stirred at 80°C overnight. Cool to room temperature, add 500ml of water, solid precipitates, filter, and wash the obtained solid with ethanol to obtain 44.1g of 4-chloro-1,8-bis(9,9-dimethyl-9H-fluoren-1-yl) Pyrene, yield 71%, HPLC purity 98.8%.

[0109] 1 HNMR(DMSO): δ8.52(d, 1H), 8.30(d, 1H), 8.15(d, 2H), 8.00(m, 2H), 7.90(m, 2H), 7.72~7.68(m, 5H) ,7.57~7.55(m,4H),7.38(m,2H),7.28(m,2H),1.69(s,12H).

[0110]

[0111] Under an argon atmosphere, 62.1 grams (100 mmol) of 4-chloro-1,8-bis(9,9-dimethyl-9H-fluoren-1-yl)pyrene, (3-phenylquinoxaline -2-yl)boronic acid 30.0g (120mmol), [1,3...

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Abstract

The present invention relates to a pyrene derivative for an organic light-emitting element, a light-emitting element material containing the pyrene derivative, and a light-emitting element, and more specifically, to a soluble organic compound having excellent color purity and high brightness and light-emitting efficiency, and an OLED device using the same. Compounds are characterized by being represented by general formula (1).

Description

technical field [0001] The present invention relates to pyrene derivatives for organic light-emitting elements, light-emitting device materials and light-emitting devices containing pyrene derivatives, and more specifically, to a soluble organic compound having excellent color purity, high brightness and luminous efficiency, and the use of the pyrene derivative. Compound OLED devices. Background technique [0002] Organic light-emitting diode (Organic Light-Emitting Diode, referred to as OLED). The light-emitting device has attracted attention because of its thin profile, high-intensity light emission at a low driving voltage, and multi-color light emission by selecting a light-emitting material. [0003] Since C.W.Tang of Kodak Company revealed that organic thin film components can emit light with high brightness, a large number of researchers in the OLED industry have done a lot of research and advancement on its application. Organic thin film light-emitting devices are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14
CPCC07D405/14C07D405/10C07D409/14C07D409/10C07D241/42C07D241/38C07D403/14C07D403/10C07D413/14C07D413/10C07D417/14C07D417/10C07D401/10C07D401/14C07D403/04C07D413/04C09K11/06C09K2211/1011C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092H10K85/622H10K85/615H10K85/624H10K85/626H10K85/657H10K85/6576H10K85/6574H10K85/6572H10K50/15H10K50/16H10K50/17H10K50/171H10K50/11
Inventor 王鹏
Owner ZHEJIANG HUADISPLAY OPTOELECTRONICS CO LTD
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