Synthesis and photoelectric properties of carbazole-based room temperature phosphorescent materials containing s/se/te heavy atoms

A technology based on carbazole-based compounds, which is applied in the field of synthesis of carbazole-based room temperature phosphorescent materials, can solve problems such as self-quenching and oxygen quenching, achieve mild synthesis conditions, narrow optical band gap, and meet test requirements

Active Publication Date: 2020-09-11
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still limitations in the design and development of tellurophene-based room-temperature phosphorescent materials. At present, there are few studies on tellurphene-based phosphorescent materials, and they are prone to self-quenching and oxygen quenching. Therefore, the design and development of new tellurphene-based room-temperature phosphorescent materials has very important research significance

Method used

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  • Synthesis and photoelectric properties of carbazole-based room temperature phosphorescent materials containing s/se/te heavy atoms
  • Synthesis and photoelectric properties of carbazole-based room temperature phosphorescent materials containing s/se/te heavy atoms
  • Synthesis and photoelectric properties of carbazole-based room temperature phosphorescent materials containing s/se/te heavy atoms

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] A D-A type carbazolyl compound PhCz-T of the present invention has a general structural formula of formula I:

[0055]

[0056] The synthetic route of PhCz-T is:

[0057]

[0058] Specifically include the following steps:

[0059] (1) Synthesis of intermediate a: Add carbazole (1.0 g, 6.0 mmol) and anhydrous tetrahydrofuran (30 mL) to 100 mL of Schlenk under nitrogen protection, and then place the reaction bottle in a cryogenic apparatus at -78 °C. At -78°C, lithium diisopropylamide (2.0M, 3.3mL) was slowly added dropwise into the reaction flask, reacted at -78°C for 1h, and then slowly returned to -40°C and stirred for 1h. Then, a tetrahydrofuran solution (2.4 g, 9 mmol) of 4-iodobenzoyl chloride was injected once at −78° C., and finally stirred overnight at room temperature. The mixture was extracted with ethyl acetate and water, dried, filtered and spin-dried. The crude product was purified by silica gel column chromatography (petroleum ether: ethyl acetate ...

Embodiment 2

[0076] A D-A type carbazolyl compound PhCz-Se of the present invention has a general structural formula of formula II:

[0077]

[0078] The synthetic route of PhCz-Se is:

[0079]

[0080] Concrete synthetic steps are:

[0081] (1) Synthesis of intermediate a: synthesized with reference to the synthetic method of the above-mentioned Example 1.

[0082] (2) Synthesis of compound PhCz-Se: In a 10 mL microwave bottle, add iodocarbazolyl intermediate (0.85 g, 2.1 mmol), selenophene unilateral tin compound (1.0 g, 3.4 mmol) and 6 mL of toluene. Oxygen was replaced under nitrogen for 20 minutes, then the catalyst tetrakistriphenylphosphine palladium (8 mg) was added, nitrogen was blown for 10 minutes, a microwave cover was sealed, and the reaction was carried out at 120° C. for 4 hours. After cooling to room temperature, extract with dichloromethane, dry over anhydrous magnesium sulfate, filter with suction, and spin dry. The mixture was purified by silica gel column chrom...

Embodiment 3

[0092] A D-A type carbazolyl compound PhCz-Te of the present invention has a general structural formula of formula III:

[0093]

[0094] The synthetic route of PhCz-Te is:

[0095]

[0096] Concrete synthetic steps are:

[0097] (1) Synthesis of intermediate a: synthesized with reference to the synthetic method of the above-mentioned Example 1.

[0098] (2) Synthesis of compound PhCz-Te: In a 10mL microwave bottle, put iodocarbazolyl intermediate (0.8g, 2.0mmol), tellurphene unilateral tin compound (1.0g, 3.0mmol) and 6mL chlorobenzene . Oxygen was replaced under nitrogen for 20 minutes, then the catalyst tetrakistriphenylphosphine palladium (8 mg) was added, nitrogen was blown for 10 minutes, a microwave cover was sealed, and the reaction was carried out at 140° C. for 4 hours. After cooling to room temperature, extract with dichloromethane, dry over anhydrous magnesium sulfate, filter with suction, and spin dry. The mixture was purified by silica gel column chroma...

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Abstract

The invention discloses a preparation method of a D-A type carbazole-based derivative and its luminescent properties, wherein the general structural formula of the D-A-type carbazole-based derivative is that the D-A type structure uses carbazole as a donor unit, and benzo The acyl group is the acceptor unit, and the three kinds of materials all have good solubility and thermal stability. The preparation method of the carbazolyl derivatives of the present invention mainly consists of 4-iodobenzoyl and five-membered heterocyclic unilateral tin compounds through Stille Preparation by coupling reaction. The preparation method provided by the invention has simple route, few steps and low production cost. More importantly, by substituting heteroatoms with different weights, the luminescent properties of this type of material are regulated, and the transition from fluorescence to phosphorescence is realized, so it has broad application prospects in the fields of organic light-emitting diodes and bioimaging.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to the background technology for the synthesis and photoelectric performance research of a carbazole room-temperature phosphorescent material containing S / Se / Te heavy atoms. Background technique [0002] Organic room-temperature phosphorescent materials have attracted extensive attention in the field of organic electroluminescence due to their characteristics of wide source, low cost, low toxicity, easy purification and easy structure modification. Among them, it has broad application prospects in the fields of data security and confidentiality, organic light-emitting diodes (OLEDs), light-emitting sensors, and biological imaging. Studies have confirmed that the long-lived D-A room temperature phosphorescent material can be obtained by reacting the donor (D) unit carbazole with the acceptor (A) unit benzoyl group and modifying the molecular structure through heavy halo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/10C07D421/10C09K11/06
CPCC07B2200/13C07D409/10C07D421/10C09K11/06C09K2211/1029C09K2211/1092C09K2211/1096
Inventor 黄辉邓祎华
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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