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Carbazole dioxazine compound

A dioxazine and compound technology, which is applied in the field of organic synthesis, can solve the problems such as the interruption of the conjugated chain and affect the luminescence performance, and achieves the effects of easy operation, good solubility and simple preparation method

Inactive Publication Date: 2015-09-09
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004]Currently, the research on carbazole-type dioxazine compounds (such as Pigment Violet 23) is limited to 3,6-substituted carbazole, when it is connected with other conjugated units It will lead to the interruption of the conjugated chain and affect its luminescent properties

Method used

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  • Carbazole dioxazine compound
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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] Put 2.2 g of N-methyl-2-amino-7-bromocarbazole, 1 g of sodium carbonate, 1 g of tetrachlorobenzoquinone, and 20 mL of o-dichlorobenzene into the reaction flask, react at 25°C for 7 h, and then add 1.5 g of benzoyl chloride, continue to react at 165 °C for 6 h, remove most of the o-dichlorobenzene after the reaction, filter, and wash thoroughly with methanol, water, and methanol in turn to obtain 2.5 g of carbazole-type dioxazine compounds, yield 87%.

[0027] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.87-7.84 (m, 2H), 7.83–7.81 (m, 2H), 7.66-7.63 (m, 2H), 7.46-7.44 (m 2H), 7.45-7.441 (m 2H), 3.82 (s, 6H); 13 C NMR (400 MHz, CDCl 3 ): δ (ppm) 164.6, 143.2, 135.5, 131.6, 128.4, 128.1, 125.7, 123.2, 114.6, 111.6, 111.4, 109.4, 107.1, 106.3, 99.4, 29.9.

Embodiment 2

[0029]

[0030] Put 2.8 g N-methyl-1-methyl-2-amino-7-iodo-8-methylcarbazole, 1 g sodium carbonate, 1.7 g tetrabromobenzoquinone, and 20 mL o-dichlorobenzene into the reaction flask After reacting at 25°C for 7 h, add 1.5 g of benzoyl chloride, continue to react at 165°C for 6 h, remove most of the o-dichlorobenzene after the reaction, filter, and wash thoroughly with methanol, water, and methanol in turn to obtain carbazole Dioxazine-like compound 3.2 g, yield 82%.

[0031] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 7.77-7.74 (m, 2H), 7.51–7.47(m, 2H), 7.36-7.33 (m, 2H), 3.82 (s, 6H), 2.34 (s, 6H), 1.97 (s , 6H); 13 C NMR (400 MHz, CDCl 3 ): δ (ppm) 164.6, 143.2, 140.5, 130.6, 129.4, 129.1, 117.6, 115.6, 115.4, 114.4, 103.3, 92.4, 89.5, 86.9, 37.4, 15.4, 12.5.

Embodiment 3

[0033]

[0034]Put 4.9 g N-butyl-2-amino-4-pentyl-6-methyl-7-bromocarbazole, 1.5 g sodium carbonate, 1.5 g chloranil, and 40 mL o-dichlorobenzene into the reaction flask After reacting at 40°C for 6 h, add 2.6 g p-toluenesulfonyl chloride, continue to react at 165°C for 6 h, remove most of the o-dichlorobenzene after the reaction, filter, and wash thoroughly with methanol, water, and methanol in turn to obtain carba The azole dioxazine compound was 4.8 g, and the yield was 81%.

[0035] 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) 8.43-8.41 (m, 2H), 8.24–8.21(m, 2H), 7.49-7.47 (m, 2H), 4.64-4.61(m, 4H), 2.67-2.65 (m, 4H) , 2.34(s6), 1.71-1.69 (m, 4H), 1.31-1.29 (m, 16H), 0.91-0.88 (t, 12H); 13 C NMR (400 MHz, CDCl 3 ): Δ (PPM) 164.6, 143.3, 135.7, 135.3, 134.2, 128.4, 127.7, 125.1, 122.3, 115.4, 114.3, 104.3, 102.3, 99.2, 58.5, 32.8, 31.4, 24.7, 14.1.

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Abstract

The invention discloses a carbazole dioxazine compound represented in formula (1) and belongs to the field of organic synthesis. The carbazole dioxazine compound is prepared from a 2, 7-position amino-carbazole derivative and halogenated benzoquinone by means of coupling and condensation reaction. The carbazole dioxazine compound has the advantages that the compound is of a heterocyclic hyperconjugation structure, a molecule of the compound is of a planar rigidity symmetrical structure, the compound can be used as violet pigment by being high in heat stability, can be applied to the fields of organic light-emitting diodes and organic semiconductors due to being high in charge transport capacity and having hole mobility which can be above 1.0E10<-6>cm<2>V<-1>s<-1>, and can be used as polymer semiconductor materials after further polymerization, thereby being quite promising in application prospect. In the formula (1) (see original text), R1 refers to C1-50 alkyl, R3 and R4 refer to H and C1-C20 alkyl and phenyl at any position respectively, R2 and X refer to halogen, and the whole molecule is of a centrosymmetric structure.

Description

technical field [0001] The invention relates to a carbazole-type dioxazine compound, which belongs to the field of organic synthesis. Background technique [0002] Carbazole and its derivatives are a class of diphenylamine molecules with an isoelectronic structure, which contain a large conjugated system and strong intramolecular electron transfer, and have strong electron-donating and hole-transporting capabilities. Based on the special rigid fused ring structure and long conjugated chain of carbazole, carbazole compounds have potential wide applications in the fields of optoelectronic materials, fuels, medicine, and chemical sensing. [0003] At present, the more common carbazole compounds are easy to introduce other functional groups at the 3-position, 6-position and 9-position for structural modification, so that the carbazole compounds exhibit many unique properties and biological activities. However, the substitution of the 2 and 7 positions of carbazole compounds sho...

Claims

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Application Information

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IPC IPC(8): C07D498/22H01L51/54
CPCC07D498/22H10K50/00
Inventor 王金良王建莉李玉宁郭利兵袁梦旗周晓楠李旭王晋
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD