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Disubstituted derivative of carboline, and preparation method and application thereof

A derivative, carboline II technology, applied in the field of organic electroluminescent materials, can solve problems such as unbalanced electron and hole transport capabilities, low luminous efficiency, and affecting the normal use of carboline derivatives, and achieve high triplet energy , high luminous efficiency and balanced transmission capacity

Inactive Publication Date: 2017-07-04
SHANGHAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the existing carboline derivatives used in organic electroluminescent materials have unbalanced electron and hole transport capabilities, which leads to low luminous efficiency and affects the normal use of carboline derivatives.

Method used

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  • Disubstituted derivative of carboline, and preparation method and application thereof
  • Disubstituted derivative of carboline, and preparation method and application thereof
  • Disubstituted derivative of carboline, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment one: the preparation of compound A-5

[0068]a) Synthesis of 2-phenyl-3-nitropyridine (a1): 5 gram 2-chloro-3-nitropyridine, 4.7 gram phenylboronic acid, 8.7 gram potassium carbonate, 0.1 gram palladium acetate, 0.4 gram triphenyl Base phosphine, 60 ml of 1,4-dioxane / distilled water (3:1) was added into a three-necked flask, and stirred under reflux for 24 hours under the protection of nitrogen. After the reaction was completed, distilled water was added to the system and stirred until the solution became clear, then extracted with ethyl acetate, washed with saturated brine, dried, concentrated, and column chromatographed to obtain 6.0 g of solid, with a yield of 93%. Mass spectrum: theoretical value m / e, 190.1; found value 190.1. 1 H-NMR (500MHz, CDCl 3 ): 8.83(1H), 8.11(1H), 7.60-7.54(2H), 7.50-7.43(3H), 7.39(1H).

[0069]

[0070] b) Synthesis of δ-carboline (a2): 5 g of 2-phenyl-3-nitropyridine was dissolved in 30 ml of triethyl phosphite, and stirr...

Embodiment 2

[0081] Embodiment two: the preparation of compound A-6

[0082] 3-(δ-carbolinyl)-phenylboronic acid pinacol ester (a4) 1g, N-(3-bromophenyl)-δ-carboline (a3) ​​0.9g, potassium carbonate 1.5g, distilled water 20ml , toluene 50ml, ethanol 10ml, palladium acetate 0.1g, triphenylphosphine 0.4g, under nitrogen protection, reflux and stir for 24h. After the reaction was completed, it was extracted with dichloromethane, washed with saturated brine, dried, concentrated, and subjected to column chromatography to obtain 1.0 g of solid A-6 with a yield of 76%. Mass spectrum: theoretical value m / e, 486.2; measured value 486.1. 1H-NMR (500MHZ, CDCl 3 ,): 8.62(2H), 8.46(2H), 7.84(2H), 7.79-7.70(6H), 7.59(2H), 7.56-7.57(4H), 7.39(2H), 7.33(2H).

[0083]

Embodiment 3

[0084] Embodiment three: the preparation of compound B-2

[0085] a) N-(6-bromo-pyridin-2-yl)-δ-carboline (a9): using 2,6-dibromopyridine and δ-carboline as raw materials, the synthesis steps are the same as a3, mass spectrum: theoretical value m / e, 323.0, 325.0; found value 323.1, 325.1.

[0086] b) Compound B-2: using 3-(δ-carbolyl)-phenylboronic acid pinacol ester (a4) and N-(6-bromo-pyridin-2-yl)-α-carboline as raw materials, The synthesis method is the same as A-5. Mass spectrum: theoretical value m / e, 487.2; measured value 487.3.

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Abstract

The invention especially relates to a disubstituted derivative of carboline, and a preparation method and application thereof, belonging to the technical field of organic electroluminescent materials. The disubstituted derivative of carboline can be used as an electron or hole transport material and is also applicable as an illuminant for luminescence as an individual luminescent layer or as a doping dye. The disubstituted derivative of carboline gives out strong fluorescent light in liquid and solid films, can form a good amorphous film and is in a high triplet-state energy level.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a carboline disubstituted derivative and its preparation method and application. Background technique [0002] With the development of display technology, the requirements for flat panel display devices are getting higher and higher. Three display technologies have emerged in recent years: plasma displays, field emission displays, and organic electroluminescent displays (OLEDs). Among them, OLED has a series of advantages such as self-luminescence, low-voltage DC drive, full curing, wide viewing angle, and rich colors. Compared with liquid crystal displays, OLED does not require a backlight source, has a large viewing angle, low power, and its response speed is 1000 times that of liquid crystal displays, but its manufacturing cost is lower than that of liquid crystal displays with the same resolution. Therefore, OLED is bound to have broad applicatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00C07D471/04C09K11/06H01L51/54
CPCC09K11/06C07D471/04C07D519/00C09K2211/1007C09K2211/1044C09K2211/1029C09K2211/1088C09K2211/1092H10K85/6572H10K50/11
Inventor 王子兴沈博文王荷丹张震赵晓宇
Owner SHANGHAI UNIV
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