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Compounds containing carbazole structural units and their preparation methods and applications

A compound and coupling reaction technology, which is applied in the field of compounds containing carbazole structural units and their preparation, can solve the problems that there is still a long way to go in practical application, and there are many problems

Active Publication Date: 2016-01-13
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, especially organic materials with excellent comprehensive indicators are in urgent need of research and development, green and red materials are developing rapidly, and can basically meet the needs of commercialization and practicality, while blue materials are in urgent need of research and development. The lifespan is much lower than the other two materials, and there are many problems, and there is still a distance from practical application, which has been a problem that has plagued OLED technology for a long time.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 4

[0110] The starting reactant 4e used in embodiment 4 is prepared according to the following method:

[0111] step 1: Synthesis

[0112]

[0113] Into a 250mL reaction bottle, put 10.0mmol of 2,7-dibromo-9-fluorenone, 22.0mmol of diphenylamine, and 0.1mmol of Pd 2 (dba) 3 , 0.5mmol of S-phos, 30mmol of sodium tert-butoxide, and then 80mL of toluene were added and reacted at 110°C for 6 hours. The system was spin-dried to obtain a black oil. After passing through a silica gel column, eluting with petroleum ether: dichloromethane = 5: 1 to obtain a brown oily product, yield: 65%

[0114] Step 2: Synthesis

[0115]

[0116] According to step 2 of the aforementioned method for preparing 1e, 1a was replaced by compound 4a to obtain the target compound. Yield: 85%.

[0117] Step 3: Synthesis

[0118]

[0119] According to step 3 of the aforementioned method for preparing 1e, 1b was replaced by 4b obtained in step 2 to obtain the target compound. Yield: 68%.

[0...

Embodiment 1

[0196] Embodiment 1, compound preparation of

[0197]

[0198] Into a 100mL reaction flask, put 2.0mmol of compound 1e obtained in step 5, 2.2mmol of p-bromoanisole, 2.6mmol of sodium tert-butoxide, 0.01mmol of palladium acetate, and 0.04mmol of tri-tert-butylphosphine, and then add 10mL of xylene, after Hartwig coupling reaction at 140°C for 8 hours, add 20mL of ethyl acetate and 20mL of water to the system, stir and separate, the aqueous phase is extracted twice with 20mL of ethyl acetate, and the organic phase is extracted with 20mL of saturated salt Washed twice with water, combined the organic phases, and spin-dried to obtain a brown solid. After passing through a silica gel column and eluting with petroleum ether: ethyl acetate = 10:1, a white solid product was obtained, with a yield of 30%.

[0199] 1 HNMR (CDCl 3 ,300MHz):δ=8.55(d,1H),8.09(d,1H),7.92-7.94(d,1H),7.75-7.81(m,2H),7.16-7.52(m,19H),6.99-7.01 (d,2H),3.83(s,3H);

[0200] Glass transition temperature T...

Embodiment 2

[0204] Embodiment 2, compound Synthesis

[0205]

[0206] According to the steps of Example 1, only p-bromoanisole was replaced by 4-bromobiphenyl to obtain a white solid product with a yield of 32%.

[0207] 1 HNMR (CDCl 3 ,300MHz):δ=8.55(d,1H),8.07-8.09(d,1H),7.92-7.94(d,1H),7.74-7.82(m,4H),7.56-7.68(m,4H),7.40 -7.52 (m, 14H), 7.31-7.36 (m, 2H), 7.12-7.28 (m, 4H).

[0208] Glass transition temperature Tg: 268°C;

[0209] UV absorption wavelength: 245nm, 355nm;

[0210] Fluorescence emission wavelength: 404nm.

[0211] 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

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Abstract

The invention discloses a compound containing a carbazole structural unit, a preparation method and application thereof. The general structural formula of the compound containing the spirofluorene structural unit is shown in Formula I. The compound represented by the formula I has correct NMR detection and can be used as an OLED monomer material, and has important application value. The main advantages of the invention are: 1) the synthesis is relatively simple; 2) it has high efficiency and stability and good glass transition temperature; 3) the device prepared by using the OLED material has low starting voltage, high luminous efficiency and good color coordinates.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a compound containing a 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 it has been wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/94C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D209/96C09K2211/1029H10K85/636H10K85/633H10K85/615H10K85/6572
Inventor 李雅敏曹建华郭剑华瑞茂
Owner SHIJIAZHUANG CHENGZHI YONGHUA DISPLAY MATERIALS CO LTD
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