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Compounds containing heteroatom bridging carbazole structural units and their preparation methods and applications

A compound and hydrogen atom technology, applied in the field of compounds containing heteroatom bridging carbazole structural units and their preparation, can solve the problems of practical application and other problems

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 heteroatom bridging carbazole structural units and their preparation methods and applications
  • Compounds containing heteroatom bridging carbazole structural units and their preparation methods and applications
  • Compounds containing heteroatom bridging carbazole structural units and their preparation methods and applications

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Experimental program
Comparison scheme
Effect test

preparation example Construction

[0158] According to the preparation method of the starting reactant 3f in Example 3, only replacing 3e with 5e, the target compound 5f was obtained. Yield: 71%.

[0159] The starting reactant 6d used in the following embodiment 6 is prepared according to the following method:

[0160] step 1: Synthesis

[0161]

[0162] According to step 1 of the aforementioned method for preparing 1d, 2,8-dibromooxyfluorene was replaced by 2,8-dibromocarbazole to obtain the target compound 6a. Yield: 46%.

[0163] Step 2: Synthesis

[0164]

[0165] According to step 2 of the aforementioned method for preparing 1d, 1a was replaced by 6a to obtain the target compound 6b. Yield: 72%.

[0166] Step 3: Synthesis

[0167]

[0168] According to step 3 of the aforementioned method for preparing 1d, 1b was replaced with 6b to obtain the target compound 6c. Yield: 85%.

[0169] Step 4: Synthesis

[0170]

[0171] According to step 4 of the aforementioned method for preparing...

Embodiment 1

[0172] Embodiment 1, compound preparation of

[0173]

[0174] Into a 100mL reaction flask, put 7.2mmol of compound 1d, 8.6mmol of bromobenzene, 0.2mmol of CuI, and 22.0mmol of 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 65%.

[0175] 1 HNMR (CDCl 3 ,300MHz):δ=8.55-8.57(d,1H),8.09-8.12(d,2H),7.94-7.96(d,1H),7.80(s,1H),7.40-7.63(m,13H),7.25 -7.29(m,4H);

[0176] Glass transition temperature Tg: 266°C;

[0177] UV absorption wavelength: 275nm, 295nm;

[0178] Fluorescence emission wavelength: 448nm. ...

Embodiment 2

[0181] Embodiment 2, compound Synthesis

[0182]

[0183] According to the steps of Example 1, only the bromobenzene was replaced by 4-methoxybromobenzene to obtain the target compound 2e with a yield of 82%.

[0184] 1 HNMR (CDCl 3 ,300MHz):δ=8.55-8.57(d,1H),8.10-8.12(d,2H),7.94-7.96(d,1H),7.63-7.66(m,3H),7.49-7.51(m,6H) ,7.41(s,1H),7.25-7.33(m,4H),6.97-6.99(d,2H),3.83(s.3H);

[0185] Glass transition temperature Tg: 289°C;

[0186] UV absorption wavelength: 285nm, 305nm, 315nm;

[0187] Fluorescence emission wavelength: 418nm.

[0188] 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

[0189]

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Abstract

The invention discloses a compound containing a heteroatom bridging carbazole structural unit, a preparation method and an application thereof. Such compounds have a general structural formula as shown in Formula I. The compound represented by the formula I has correct NMR detection. Based on the fact that there are few researches on blue light materials at the present stage, and there is a lack of high-efficiency and high-stability blue light-emitting materials, a series of OLED blue light-emitting materials containing spirofluorene structures are provided. This kind of compound has easy-to-obtain raw materials, simple preparation and high overall yield, and has important application value for researching the 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 heteroatom bridging carbazole structural unit, a preparation method and application thereof. Background technique [0002] For 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 sour...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/048C07D495/04C07D487/04C07F9/6561C09K11/06H01L51/54
CPCC09K11/06C07D487/04C07D491/048C07D495/04C07F9/6561C09K2211/1007C09K2211/1029C09K2211/1092C09K2211/1088H10K85/615H10K85/631H10K85/6572H10K85/657
Inventor 郭剑隋岩曹建华
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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