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9-alkyl alkenyl-2,7-diaryl fluorene derivate and application of 9-alkyl alkenyl-2,7-diaryl fluorene derivate

A technology of diaryl fluorene and alkyl alkenyl, which is applied in the field of organic optoelectronic materials, can solve the problems affecting the light color purity and stability of devices, and achieves improved glass transition temperature, good thermal stability, and high glass transition. Effects of temperature and decomposition temperature

Active Publication Date: 2012-11-21
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The blue luminescent materials reported in the past usually have long-wave emission, and the long-wave emission intensity will change with time and external electric field, which affects the light color purity and stability of the device
Therefore, the development of new blue light-emitting materials is an important topic, and 9-alkenyl alkenyl-2,7-diarylfluorene blue light-emitting materials have not been reported yet

Method used

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  • 9-alkyl alkenyl-2,7-diaryl fluorene derivate and application of 9-alkyl alkenyl-2,7-diaryl fluorene derivate
  • 9-alkyl alkenyl-2,7-diaryl fluorene derivate and application of 9-alkyl alkenyl-2,7-diaryl fluorene derivate
  • 9-alkyl alkenyl-2,7-diaryl fluorene derivate and application of 9-alkyl alkenyl-2,7-diaryl fluorene derivate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of 9-butylene-2,7-bis(1-naphthyl)fluorene (4,2,7-D(2Np)FBu)

[0045]

[0046] Step 1: Preparation of 2,7-DPNpFK

[0047] Add 2,7-dibromofluorenone (6.8g, 0.02mol), 4-phenyl-1-naphthaleneboronic acid (11.4g, 0.046mol), 74g toluene, 2M potassium carbonate (16.6g, 0.12mol) solution Into the three-necked flask, add Pd (PPh 3 ) 4 (460mg, 0.4mmol), tetrabutylammonium bromide (0.39g, 1.2mmol); Under the protection of nitrogen, react at 85°C for 3hr; after cooling to room temperature, let stand to separate layers, the lower layer is the organic phase, and wash the organic phase with water until Neutral; dried over anhydrous sodium sulfate, filtered; after removing the organic solvent under reduced pressure, beating with methanol; after suction filtration, 11.3 g of yellow particles (the yellow particles were 2,7-DPNpFK) were obtained, with a yield of 96%.

[0048] Step 2: Preparation of 2,7-DPNpFBu-A

[0049] Add 2,7-DPNpFK (5.8g, 0.01mol) and 72gTHF...

Embodiment 2

[0052] Example 2: Synthesis of 9-butylene-2,7-bis(4-biphenyl)fluorene (3,2,7-DBFBu)

[0053]

[0054] Step 1: Preparation of 2,7-DBFK

[0055] Add 2,7-dibromofluorenone (15.0g, 0.04mol), phenylboronic acid (13.0g, 0.11mol), 148g toluene, and 2M potassium carbonate (36.8g, 0.26mol) solution into a three-necked flask to replace nitrogen After adding Pd (PPh 3 ) 4 (920mg, 0.8mmol), tetrabutylammonium bromide (0.78g, 2.4mmol); under the protection of nitrogen, react at 85°C for 3h; after cooling to room temperature, let stand to separate layers, the lower layer is the organic phase, wash the organic phase with water until Neutral; dried over anhydrous sodium sulfate, filtered; after removing the organic solvent under reduced pressure, beating with methanol; after suction filtration, 13.7 g of yellow particles (the yellow particles were 2,7-DBFK) were obtained, with a yield of 93%.

[0056] Step 2: Preparation of 2,7-DBFBu-A

[0057] Add 2,7-DBFK (7.0g, 0.02mol) and 144gTHF ...

Embodiment 3

[0060] Example three: 9-butylene-2,7-bis(4-biphenyl)fluorene (3) photoluminescence spectrum measurement of organic optoelectronic material: 9-butylene-2,7-bis(4-biphenyl) Phenyl) fluorene (3) dubbed 5*10 -5 The dichloromethane dilute solution of M was measured by JV-3150 visible spectrometer and RF-530XPC fluorescence spectrometer, and the photoluminescence spectrum was measured at the maximum absorption wavelength of ultraviolet absorption. The absorption wavelengths of compound 3 are 375nm and 326nm, and the maximum fluorescence emission wavelength is 458nm. (see attached Figure 11 , attached Figure 12 )

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Abstract

The invention relates to the technical field of organic optoelectronic materials, in particular to a 9-alkyl alkenyl-2,7-diaryl fluorene derivate and application of the 9-alkyl alkenyl-2,7-diaryl fluorene derivate to organic electroluminescent materials. The 9-alkyl alkenyl-2,7-diaryl fluorene derivate has the structural formula shown as the accompanying drawing, R1 is aryl or heteroaryl, R2 is aryl or heteroaryl, and R3 is C3 to C12 alkyls. The 9-alkyl alkenyl fluorene derivate provided by the invention has the advantages that an alkyl chain is introduced, the glass-transition temperature of materials is effectively improved, and good light color purity and luminous efficiency are realized during the application to blue organic electroluminescent materials.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a 9-alkylenyl-2,7-diarylfluorene derivative and its application in organic electroluminescent materials. Background technique [0002] As a new generation of display technology, organic electroluminescent materials (OLED) have the following characteristics: a wide range of material selection, which can realize any color display from red to blue; low driving voltage, only 3-12V DC voltage; luminous brightness and luminous High efficiency; wide luminous viewing angle, fast response speed; in addition, it has the advantages of being ultra-thin and can be made on a flexible panel. [0003] The research on organic electroluminescent materials first began in the 1960s, but has not been paid attention to by people. Until 1987, Tang et al. from Eastern Kodak Company invented the device with a sandwich structure, using an organic small molecule material-8-hydroxyq...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/567C07C13/60C07C13/58C07C13/72C07C13/66C07C211/61C07C211/54C07D209/86C07D271/107C07D333/08C07D213/06C07D215/06C09K11/06
Inventor 石宇张学衡王培培董鹏超董凯徐凯
Owner VALIANT CO LTD
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