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A kind of carbazole dioxazine compound

A technology of dioxazine and compounds, applied in the field of organic synthesis, can solve problems such as interruption of conjugated chains and affecting luminescence performance, and achieve the effects of easy operation, good solubility and good thermal stability

Inactive Publication Date: 2017-06-16
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] At present, the research on carbazole-type dioxazine compounds (such as Pigment Violet 23) is limited to the 3, 6-substituted carbazole, which will lead to the interruption of the conjugated chain when it is connected with other conjugated units, affecting its luminescent properties

Method used

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  • A kind of carbazole dioxazine compound
  • A kind of carbazole dioxazine compound
  • A kind of carbazole dioxazine compound

Examples

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 is completed, 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 is completed, 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, 122.3, 115.4,114.9, 114.3, 104.3, 99.2, 58.5, 32.6, 31.4, 24.7, 14.1.

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Abstract

The invention discloses a carbazole-type dioxazine compound represented by formula (1), which belongs to the field of organic synthesis. The compound is prepared from 2,7-position aminocarbazole derivatives and halogenated benzoquinone through coupling and condensation reactions. The compound is a heterocyclic hyperconjugated structure, the molecule is a planar rigid symmetrical structure, has good thermal stability, can be used as a purple pigment, and has good charge transport ability, and the hole mobility can reach 1.0E10‑6cm2V‑1s‑ 1 or more, can be applied to the field of organic light emitting diodes and organic semiconductors, and can be used as polymer semiconductor materials after further polymerization, and has broad application prospects. (1) Among them: R1 is C1-50 alkyl; R3 and R4 are H, C1-C20 alkyl and phenyl at any position respectively; R2 is halogen; X is halogen; the whole molecule has 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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Patent Type & Authority Patents(China)
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