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Blue light-emitting material

A technology of the same compound, applied in the field of blue light-emitting materials, can solve problems such as poor preparation or performance

Inactive Publication Date: 2014-12-24
GUANMAT OPTOELECTRONICS MATERIALS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] where R is a linker with 6-50 carbon atoms, but its preparation or performance is not good

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0119] Example 1. Synthesis of Compound 10:

[0120] .

[0121] Synthesis of intermediate 3,6-diboronate-5,8-diphenyltriphenylene: In a 100 mL three-necked flask with a thermometer and a condenser tube, add 2.15 g (4 mmol) of 3,6-dibromo-5,8-diphenyltriphenylene in sequence, pinacol diboronate 2.54g (10 mmol), 0.2g (0.2 mmol) of tribenzylideneacetone dipalladium, 0.25g (0.6mmol) of S-phos, 1.17g (12 mmol) of potassium acetate, 20ml of toluene, replaced with nitrogen, heated to reflux for reaction 16h. Cool to room temperature, filter, collect the filtrate, use a short column of silica gel, use pure n-hexane:dichloromethane=4:1 as the mobile phase, and receive 1.58g (65%) of white solid, MS=612.

[0122] Synthesis of the final product: In a 100 mL three-neck flask with a thermometer and a condenser tube, add 2.00 g (3.16 mmol) of 3,6-diboronate-5,8-diphenyltriphenylene in sequence, 9-Bromo-10-(2-naphthyl)anthracene 2.42g (6.32 mmol), Pd(PPh 3 ) 4 0.2g (0.16 mmol...

Embodiment 2

[0123] Example 2. Synthesis of Compound 21:

[0124] .

[0125] Synthesis of Intermediate M1: In a 250 mL three-necked flask with a thermometer and a condenser tube, add 6.94 g (18.96 mmol) of 3,6-dibromophenanthrenequinone, 4.18 g (19.9 mmol) of dibenzyl ketone, and 1.78 g (30.48 mmol) of KOH ), methanol 120ml, heated to reflux for 2h. The reaction was monitored by TLC plate until complete. Cool to room temperature, filter, wash the filter residue with methanol, and filter to obtain the desired product. 6.4 g (62.5%) of a brown solid is received; it is directly used in the next reaction without purification.

[0126] Synthesis of Intermediate M2: In a 100 mL three-necked flask with a thermometer and a condenser tube, 4.5 g (8.325 mmol) of M1, 1.8 g (18.3 mmol) of trimethylsilylacetylene, and 45 ml of o-xylene were sequentially added, and the temperature was raised to reflux for 12 hours. Cooled to room temperature, filtered, the filtrate was precipitated with metha...

Embodiment 3

[0130] Example 3. Synthesis of Compound 22:

[0131] .

[0132] Synthesis of intermediate M6: In a 100 mL three-necked flask with a thermometer and a condenser tube, add 14.8 g (109 mmol) of p-cymeniline, 19.2 g (72.87 mmol) of 4-bromodibenzothiophene, and 1 g of dipalladium ( 1.09 mmol), BINAP 1.35g (21.8mmol), sodium tert-butoxide 13.9g (145 mmol), toluene 180ml, nitrogen replacement, heated to reflux for 3h. Cool to room temperature, filter, collect the filtrate, use a short column of silica gel, use pure n-hexane: dichloromethane = 4:1 as the mobile phase, and receive 18.9 g (79%) of a white solid.

[0133] Synthesis of the final product: In a 100 mL three-necked flask with a thermometer and a condenser tube, add M6 0.66g (2.1mmol), M3 0.538g (1 mmol), tribenzylideneacetone dipalladium 0.048g (0.05 mmol), P(t- 0.16 g (0.2 mmol) of Bu)3, 0.38 g (4 mmol) of sodium tert-butoxide, 25 ml of toluene, replaced with nitrogen, and heated to reflux for 16 hours. Cool to r...

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Abstract

The invention discloses a blue organic semiconductor (I) as shown in the specification. A benzophenanthrene derivative is taken as a main core, and electron holes and electronic condensed aromatic heterocycle are connected in a chemical bonding manner. The material is excellent in thermal resistance and light emitting property with high efficiency and a long service life, and a dark blue organic light emitting device with a long service life is obtained when the material is used in a light-emitting layer of an organic light-emitting diode.

Description

technical field [0001] The invention relates to an organic light-emitting material and its application in an organic light-emitting device, in particular to a blue organic semiconductor material, which can be applied to an organic light-emitting OLED device to improve device performance. Background technique [0002] Organic semiconductor materials are new types of optoelectronic materials. Its large-scale research originated in 1977 when Hideki Shirakawa, A. Heeger and A. McDiamid jointly discovered doped polyacetylene with a conductivity up to copper level. Subsequently, in 1987, C. Tang of KodaK Company invented the organic small molecule light-emitting diode (OLED), and in 1990, R. Friend and A. Holmes of Cambridge University invented the polymer light-emitting diode P-OLED, and in 1998, S. Forrest and M. Thomson invented a more efficient organic phosphorescent light-emitting diode PHOLED. Because organic semiconductor materials have a structure that can be easily adjus...

Claims

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Application Information

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IPC IPC(8): C07C15/38C07C13/66C07C1/32C07C25/22C07C17/263C07D307/91C07D333/76C07D519/00C09K11/06H01L51/54
Inventor 李晓常洪海兵
Owner GUANMAT OPTOELECTRONICS MATERIALS INC
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