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Compounds containing carbon-bridged carbazole structural units and their preparation methods and applications

A compound and organic technology, applied in the field of compounds containing carbon-bridged carbazole structural units and their preparation, can solve the problems such as the distance of practical application

Active Publication Date: 2016-06-22
SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently known materials with practical value and potential are still very limited. In particular, organic materials with excellent comprehensive indicators are in urgent need of research and development. Green materials are developing the fastest and can basically meet the needs of commercialization and practicality. Red and blue materials There are many problems, and there is still a distance from practical application

Method used

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  • Compounds containing carbon-bridged carbazole structural units and their preparation methods and applications
  • Compounds containing carbon-bridged carbazole structural units and their preparation methods and applications
  • Compounds containing carbon-bridged carbazole structural units and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0136] Embodiment 1, compound preparation of

[0137]

[0138] Into the 100mL reaction flask, drop into the K 2 CO 3 and 20 mL of xylene, and then heated to 140° C. for reflux reaction for 6 hours. Add 30 mL of ethyl acetate and 30 mL of water to the system, stir and separate the liquids, extract the aqueous phase twice with 30 mL of ethyl acetate, wash the organic phase twice with 30 mL of saturated brine, combine the organic phases, and spin dry to obtain a yellow solid. After passing through a silica gel column and eluting with petroleum ether:dichloromethane=10:1, a white solid product was obtained, with a yield of 45%.

[0139] 1 HNMR (CDCl 3 ,300MHz):δ=8.85(s,1H),8.55-8.57(d,2H),8.09-8.12(m,3H),7.01-7.19(m,4H),7.94-7.96(d,1H),7.29 -7.45(m,15H),1.87-1.92(t,4H),1.24-1.29(m,8H),0.86-0.92(t,6H);

[0140] Glass transition temperature Tg: 287°C;

[0141] UV absorption wavelength: 255nm, 318nm;

[0142] Fluorescence emission wavelength: 454nm.

[0143] As can be s...

Embodiment 2

[0144] Embodiment 2, compound Synthesis

[0145] According to the steps of Example 1, only bromobenzene was replaced by 4-bromobiphenyl to obtain the target compound with a yield of 72%.

[0146] 1 HNMR (CDCl 3 ,300MHz):δ=8.87(s,1H),8.55-8.57(d,2H),8.09-8.12(m,3H),7.01-7.19(m,4H),7.92-7.94(d,1H),7.76 -7.79(d,2H),7.63-7.68(m,4H),7.29-7.45(m,13H),1.87-1.92(t,4H),1.24-1.29(m,8H),0.86-0.92(t, 6H).

[0147] Glass transition temperature Tg: 265°C;

[0148] UV absorption wavelength: 265nm, 315nm;

[0149] Fluorescence emission wavelength: 446nm.

[0150] As can be seen from the above, the structure of the white solid product is correct, and it is a compound shown in formula I

Embodiment 3

[0151] Embodiment 3, compound Synthesis

[0152]

[0153] In the 100mL reaction bottle, drop 0.74mmol of 3f, 0.81mmol of phenylboronic acid, 2.96mmol of sodium carbonate, 0.02mmol of Pd(PPh 3 ) 4 , and then put into 20mL of toluene, 5mL of ethanol and 5mL of water, and react at 100°C for 8 hours. Add 20 mL of saturated brine and 20 mL of ethyl acetate to the system, stir and separate the liquids, extract the aqueous phase twice with 20 mL of ethyl acetate, wash the organic phase twice with 20 mL of saturated brine, combine the organic phases, and spin dry to obtain a black solid . After passing through a silica gel column, washing with petroleum ether: dichloromethane=6:1 to obtain a white solid product, yield: 68%

[0154] 1 HNMR (CDCl 3 ,300MHz):δ=8.83(s,1H),8.51-8.53(d,2H),8.09-8.12(m,2H),7.01-7.94(m,26H),1.82-1.92(t,4H),1.24 -1.26(m,8H),0.88-0.92(t,6H).

[0155] Glass transition temperature Tg: 266°C;

[0156] UV absorption wavelength: 245nm, 315nm;

[0157] ...

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Abstract

The invention discloses a compound containing a carbon-bridged carbazole structural unit and a preparation method thereof. Such compounds have a general structural formula as shown in Formula I. The compound shown in the formula I is correct in NMR detection. The present invention provides a series of OLED blue light-emitting materials containing spirofluorene structures based on the fact that there is little research on blue-light materials at the present stage, and there is a lack of high-efficiency and high-stability blue-light emitting materials. This type of compound has easy to obtain raw materials, simple preparation and high overall yield, and has important application value for the research progress and application of blue light materials.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a compound containing a carbon-bridged carbazole structural unit, a preparation method and an application thereof. Background technique [0002] Organic electroluminescence (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, 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/94C07F9/53C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D209/94C07F9/572C09K2211/1029H10K85/631H10K85/6572
Inventor 郭剑隋岩曹建华
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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