Boronic acid or boronic acid ester or method for producing polycyclic aromatic compound or oligomer of polycyclic aromatic compound by using same

A polycyclic aromatic compound technology, applied in the field of boronic acid and boronic acid ester, can solve the problems of lower yield, lower product selectivity, lower target product yield and the like

Pending Publication Date: 2018-05-11
KWANSEI GAKUIN EDUCTIONAL FOUND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are the following problems: (1) For reasons such as the heat of reaction generated in the process of adding similarly highly reactive boron tribromide to a highly reactive organolithium intermediate, a local superheated state sometimes occurs, especially Sometimes the yield decreases when the reaction scale is increased; (2) the boron compound of the cyclization precursor is also often unstable, so it is necessary to continuously carry out the intramolecular cyclization reaction as the next step reaction without separation and purification, and sometimes the final product (3) As a result, the selectivity of the product obtained is low, more purification steps are required for high purity, and the yield of the target product is also reduced

Method used

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  • Boronic acid or boronic acid ester or method for producing polycyclic aromatic compound or oligomer of polycyclic aromatic compound by using same
  • Boronic acid or boronic acid ester or method for producing polycyclic aromatic compound or oligomer of polycyclic aromatic compound by using same
  • Boronic acid or boronic acid ester or method for producing polycyclic aromatic compound or oligomer of polycyclic aromatic compound by using same

Examples

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Embodiment

[0262] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to them. First, a synthesis example of boric acid or boric acid ester will be described below.

Synthetic example (1

[0263] Synthesis Example (1): Synthesis of Compound (1-1-98)

[0264]

[0265] The flask containing Intermediate 1 (15 g) and toluene (300 ml) was heated to 70° C. under a nitrogen atmosphere to completely dissolve Intermediate 1 . After the flask was cooled to -20°C, tetramethylethylenediamine (20.8 g) and a 1.00 M mixed solution of sec-butyllithium in cyclohexane and n-hexane (89 ml) were added. After heating to 0°C and stirring for 3 hours, add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (33.3g), and reflux for 1 hour . Water and toluene were added for liquid separation, and the solvent in the organic layer was distilled off under reduced pressure. The obtained solid was washed with Solmix A-11 (trade name: Japan Alcohol Trading Co., Ltd.), dissolved in toluene, and left standing at 0° C. for 1 hour. The deposited precipitate was separated by filtration, and the filtrate was passed through a silica gel column (eluent: toluene / heptane=1 / 5 mixed solvent (volume...

Synthetic example (2

[0269] Synthesis Example (2): Synthesis of Compound (1-3-139)

[0270]

[0271] A flask charged with 1-bromo-2,6-difluorobenzene (85.4g), phenol (100g), potassium carbonate (244.7g) and N-methyl-2-pyrrolidone (NMP, 300ml) was placed under a nitrogen atmosphere The temperature was raised to 180° C. and stirred for 22 hours. After the reaction was completed, potassium carbonate was separated by filtration at 150° C., and the solvent of the filtrate was distilled off under reduced pressure. The obtained solid was dissolved in toluene and passed through a silica gel short-pass column (eluent: toluene). After the solvent was distilled off under reduced pressure, the obtained solid was washed with heptane to obtain Intermediate 2 (126.6 g) as a white solid.

[0272]

[0273] To the flask charged with Intermediate 2 (103 g) and tetrahydrofuran (500 ml) was added a 1.29 M tetrahydrofuran solution (351 ml) of isopropylmagnesium chloride·lithium chloride complex at room temperat...

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Abstract

The present invention relates to a boronic acid or a boronic acid ester or a method for producing a polycyclic aromatic compound or an oligomer of polycyclic aromatic compound by using the same. A boronic acid compound that is effective to manufacture the polycyclic aromatic compound and a method for manufacturing the polycyclic aromatic compound by using the boronic acid compound are provided. The boronic acid compound is manufactured by acting the acid on the compound represented by a following formula (1). In the formula, the A, B and C rings are independently aromatic rings or heteroaromatic rings, Y1 is any esterified -B(OH)2, X1 and X2 are -O-, >N-Ar(Ar is aryl group and the like), -S- or -Se-.

Description

technical field [0001] The present invention relates to the ability to manufacture polycyclic aromatic compounds or polycyclic aromatic polymer compounds (hereinafter also referred to as polycyclic aromatic compounds) used in organic electroluminescent devices, organic field effect transistors, and organic thin film solar cells, as well as display devices and lighting devices. Boronic acids and boronate esters of cycloaromatic compounds, etc.). Background technique [0002] Conventionally, various researches have been carried out on display devices using electroluminescent light-emitting devices because they can save power and be thinner. Furthermore, organic electroluminescent devices formed of organic materials have been actively researched because they are easy to reduce in weight and increase in size. Research. In particular, the development of organic materials with light-emitting characteristics such as blue, one of the three primary colors of optics, and the developm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F5/04C09K11/06H01L51/30H01L51/46H01L51/54
CPCC07F5/02C07F5/025Y02E10/549C07F5/022
Inventor 畠山琢次今井宏之马场大辅山田博田岛晶夫王国防
Owner KWANSEI GAKUIN EDUCTIONAL FOUND
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