1,ω-bis(3,6-diarylcarbazolyl)-alkane and its preparation method

A technology of diarylcarbazolyl and naphthylcarbazolyl is applied in the field of 1,ω-bis-alkane and its preparation, and can solve the problems of reducing the external quantum efficiency to only

Inactive Publication Date: 2020-07-07
SHENZHEN UNIV
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Problems solved by technology

However, the triplet excited state energy of CBP is only 2.56eV. If it is doped with a blue phosphorescent material with a high triplet excited state energy (>2.65eV), the phenomenon of returning energy to the main luminescent material will occur, making the external quantum of the device Efficiency drops to only (5.7±0.3)% [Appl.Phys.Lett., 79, 2082(2001)]

Method used

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  • 1,ω-bis(3,6-diarylcarbazolyl)-alkane and its preparation method
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  • 1,ω-bis(3,6-diarylcarbazolyl)-alkane and its preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] (Ⅰ) Synthesis of 3,6-diphenyl-9H-carbazole, the reaction formula is as follows:

[0032]

[0033] Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol), NaBPh4 (2.736g, 8mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5mmol), chlorinated into a 250mL three-necked flask Palladium (0.05g, 0.25mmol), 2M sodium carbonate solution 30ml, acetone 120ml, refluxed under nitrogen atmosphere for 36h. The acetone was evaporated, the aqueous layer was extracted with dichloromethane, the extract was washed with water and dried over anhydrous magnesium sulfate, and separated by silica gel column chromatography to obtain a white flocculent product 3,6-diphenyl-9H-carbazole (2.3g, yields: 89%), the eluent is petroleum ether: methylene chloride = 2:1. Melting point: 177.1°C.

[0034] The test results of 3,6-diphenyl-9H-carbazole are as follows:

[0035] Hydrogen spectrum:

[0036] 1 H NMR(CDCl 3 ,400MHz),δ(ppm):8.34(s,2H),7.73(d,J=7.6Hz,4H),7.71-7.68(m,2H),7.49(t,J=7.5Hz,6H),7.36 (t, J=7.4 Hz, 2H). ...

Embodiment 2

[0057] (Ⅰ) Synthesis of 3,6-diphenylmethyl-9H-carbazole, the reaction formula is as follows:

[0058]

[0059] Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol), 4-methylphenylboronic acid (2.72g, 18mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5 mmol), palladium chloride (0.05g, 0.25mmol), 30ml of 2M sodium carbonate solution, 120ml of acetone, reflux for 36h under nitrogen. The acetone was evaporated, the aqueous layer was extracted with dichloromethane, the extract was washed with water and dried with anhydrous magnesium sulfate, and separated by silica gel column chromatography to obtain a white flocculent product 3,6-benzyl-9H-carbazole (2.3g , Yields: 90%), the eluent is petroleum ether: methylene chloride = 2:1. Melting point: 204.0°C.

[0060] The test results of 3,6-Diphenylmethyl-9H-carbazole are as follows:

[0061] Hydrogen spectrum:

[0062] 1 H NMR(CDCl 3 ,400MHz),δ(ppm):8.46(s,2H),7.82-7.76(m,6H),7.57(s,2H),7.43(d,J=7.9Hz,4H),2.58(s,6H) .

[0063] Carbon spectrum:

[00...

Embodiment 3

[0083] (Ⅰ) Synthesis of 3,6-Diαnaphthyl-9H-carbazole

[0084]

[0085] Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol), α-naphthylboronic acid (3.096g, 18mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5mmol) into a 250mL three-necked flask ), palladium chloride (0.05g, 0.25mmol), 2M sodium carbonate solution 30ml, acetone 120ml, reflux for 36h under nitrogen atmosphere. The acetone was evaporated, and the aqueous layer was extracted with dichloromethane. The extract was washed with water and dried with anhydrous magnesium sulfate. The white flocculent product 3,6-diαnaphthyl-9H-carbazole (3.0g) was separated by silica gel column chromatography. , Yields: 90%), the eluent is petroleum ether: methylene chloride = 2:1. Melting point: 139.4°C.

[0086] The test results of 3,6-diαnaphthyl-9H-carbazole are as follows:

[0087] Hydrogen spectrum:

[0088] 1 H NMR(CDCl 3 ,400MHz),δ(ppm):8.23(s,1H),8.19(s,2H),7.99(d,J=8.5Hz,2H),7.91(d,J=8.0Hz,2H),7.87-7.85 (m, 2H), 7.58 (s, 4H), 7.56-7.48 (...

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Abstract

The invention relates to 1,omega-bis(3,6-diaryl carbazolyl)-alkane. The 1,omega-bis(3,6-diaryl carbazolyl)-alkane is of a structure (described in the specification), wherein Ar is phenyl, p-methylphenyl, alpha naphthyl or beta naphthyl; and R is ethyl, propyl, butyl or benzyl. The invention also provides a preparation method of 1,omega-bis(3,6-diaryl carbazolyl)-alkane.

Description

Technical field [0001] The invention relates to a 1,ω-bis(3,6-diarylcarbazolyl)-alkane and a preparation method thereof. Background technique [0002] In 1987, Eastern Kodak Company CWTang et al. invented a sandwich structure device in the literature (CWTang, SAanslyke Appl. Phys. Lett. 1987, 51, 913) and the patent US4356429, which used high fluorescence efficiency, electron transport characteristics and energy Use vacuum-coated 8-hydroxyquinoline aluminum (Alq3) and hole transporting aromatic diamine (diamine) to make uniform and dense high-quality thin films, and make organic EL devices to make organic electroluminescent materials The research work with devices has entered a practical era. In 1990, Friend and others of the Cavendish Laboratory at the University of Cambridge in the United Kingdom reported on the phenomenon of polymer electroluminescence at low voltage, which opened a new field of polymer flat panel display research; in 1992, Heeger and others of Pennsylvania S...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C09K11/06
Inventor 牛芳芳曾鹏举连加荣李晓聪
Owner SHENZHEN UNIV
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