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Benzophenothiazine derivative and preparation method thereof

A technology of benzophenothiazine and derivatives, which is applied in the field of organic photoelectric functional materials, can solve the problems of resource scarcity, limited development and application, and high price, and achieve the goal of broadening the spectral response range, improving charge transfer, and low production cost. Effect

Pending Publication Date: 2021-12-28
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the scarcity and high price of precious metals (such as iridium, platinum, etc.) in metal complex phosphorescent materials, their further development and application are greatly limited.

Method used

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  • Benzophenothiazine derivative and preparation method thereof
  • Benzophenothiazine derivative and preparation method thereof
  • Benzophenothiazine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] The synthetic route is as follows:

[0041]

[0042] A mixed solution of 2-aminobenzenethiol (0.75 g, 6 mmol) and 1-tetralone (0.584 g, 4 mmol) in DMSO (16.0 mL) was stirred at 110° C. in air for 24 hours. Upon completion, the reaction mixture was diluted with ethyl acetate (64.0 mL) and filtered. The volatiles were removed in vacuo to give crude product. Further separation and purification by silica gel column chromatography (EtOAc / petroleum ether) gave benzophenothiazine 1. Yield: 87%. 1 H NMR (400MHz, Chloroform-d) δ9.58(s,2H),7.89–7.80(m,2H),7.76–7.69(m,2H),7.64(dd,J=7.4,1.5Hz,2H), 7.53–7.42(m,4H),7.29(dd,J=7.4,0.5Hz,2H),7.19–7.15(m,1H),7.15–7.01(m,7H).

[0043]

[0044] In a round bottom flask was added benzophenothiazine 1 (1.246g, 5mmol), 4-bromobenzonitrile (1.092g, 6mmol), sodium tert-butoxide (2.76g, 15mmol), tris(dibenzylideneacetone) Dipalladium (92mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (0.146g, 0.5mmol), toluene 25mL....

Embodiment 2

[0046]

[0047] The synthetic route is as follows:

[0048]

[0049]A mixed solution of 2-aminobenzenethiol (0.75 g, 6 mmol) and 1-tetralone (0.584 g, 4 mmol) in DMSO (16.0 mL) was stirred at 110° C. in air for 24 hours. Upon completion, the reaction mixture was diluted with ethyl acetate (64.0 mL) and filtered. The volatiles were removed in vacuo to give crude product. Further separation and purification by silica gel column chromatography (EtOAc / petroleum ether) gave benzophenothiazine 1. Yield: 87%. 1 H NMR (400MHz, Chloroform-d) δ9.58(s,2H),7.89–7.80(m,2H),7.76–7.69(m,2H),7.64(dd,J=7.4,1.5Hz,2H), 7.53–7.42(m,4H),7.29(dd,J=7.4,0.5Hz,2H),7.19–7.15(m,1H),7.15–7.01(m,7H).

[0050]

[0051] In a round bottom flask was added benzophenothiazine 1 (1.246g, 5mmol), (4-bromophenyl)[bis(2,4,6-trimethylphenyl)]borane (2.424g, 6mmol) , sodium tert-butoxide (2.76g, 15mmol), tris(dibenzylideneacetone) dipalladium (92mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (0...

Embodiment 3

[0053]

[0054] The synthetic route is as follows:

[0055]

[0056] A mixed solution of 2-aminobenzenethiol (0.75 g, 6 mmol) and 1-tetralone (0.584 g, 4 mmol) in DMSO (16.0 mL) was stirred at 110° C. in air for 24 hours. Upon completion, the reaction mixture was diluted with ethyl acetate (64.0 mL) and filtered. The volatiles were removed in vacuo to give crude product. Further separation and purification by silica gel column chromatography (EtOAc / petroleum ether) gave benzophenothiazine 1. Yield: 87%. 1 H NMR (400MHz, Chloroform-d) δ9.58(s,2H),7.89–7.80(m,2H),7.76–7.69(m,2H),7.64(dd,J=7.4,1.5Hz,2H), 7.53–7.42(m,4H),7.29(dd,J=7.4,0.5Hz,2H),7.19–7.15(m,1H),7.15–7.01(m,7H).

[0057]

[0058] Add benzophenothiazine 1 (1.246g, 5mmol), 5-bromo-1,3-benzenedinitrile (1.246g, 6mmol), sodium tert-butoxide (2.76g, 15mmol), three ( Dibenzylideneacetone) dipalladium (92mg, 0.1mmol), tri-tert-butylphosphine tetrafluoroborate (0.146g, 0.5mmol), toluene 25mL. Under the protec...

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Abstract

The invention relates to a novel benzophenothiazine derivative and a preparation method thereof. According to the invention, benzophenothiazine is used as an electron donating group, an electron acceptor group is covalently bonded on a nitrogen atom of phenothiazine, and the structural general formula is shown as a formula a or b; a twisted molecular skeleton is formed between the acceptor group in the material and a benzophenothiazine unit, and separated highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are formed, so that the novel benzophenothiazine derivative has efficient intramolecular charge transfer transition, and the separated HOMO and LUMO tracks are beneficial to reduction ofdelta EST, so that effective thermally activated delayed fluorescence is generated; the raw materials are common and easy to obtain, and the production cost is low. and the benzophenothiazine derivative disclosed by the invention is applied to organic electroluminescent devices and has high luminous efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, and specifically relates to a class of benzophenothiazine derivatives and a preparation method. Background technique [0002] Organic light-emitting diode (OLED) is a device that uses organic materials to convert electrical energy into light. Organic light-emitting materials are the basic core material of flexible display technology. Flexible OLED is the basis for realizing curved display and even future flexible display. OLED has the characteristics of self-luminous display, which makes its contrast, black field performance, color gamut, response speed, and viewing angle all revolutionary compared with the current mainstream LED liquid crystal display in the market. As a new generation of display technology, OLED has a simple display structure , Consumables are environmentally friendly, and the OLED display is flexible and rollable, which is more convenient fo...

Claims

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Application Information

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IPC IPC(8): C07D279/36C07D417/10C07F5/02C09K11/06
CPCC07D279/36C07D417/10C07F5/027C09K11/06C09K2211/1037C09K2211/1059C09K2211/1014C09K2211/1007
Inventor 许文娟张清源王鹤然房维佳密保秀黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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