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Polymerizable liquid crystal composition, polarized light-emitting coating material, novel naphtholactam derivative, novel coumarin derivative, novel nile red derivative, and novel anthracene derivative

A technology of polymerizable liquid crystals and naphthalenolactams, which can be used in luminescent coatings, naphtholactam dyes, liquid crystal materials, etc., and can solve the problems of no teaching and no records

Inactive Publication Date: 2013-11-20
ADEKA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Patent Document 6 discloses a system for authenticating an article by detecting fluorescent or phosphorescent radiation, wherein the fluorescent or phosphorescent radiation is polarized fluorescent or phosphorescent radiation emitted by irradiating a fluorescent substance with radiation, Patent Document 7 discloses an optical component for preventing counterfeiting using an alignment fluorescent dye, but neither describes nor teaches the polarized light-emitting element using a polymerizable liquid crystal compound and a colorant of the present invention.

Method used

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  • Polymerizable liquid crystal composition, polarized light-emitting coating material, novel naphtholactam derivative, novel coumarin derivative, novel nile red derivative, and novel anthracene derivative
  • Polymerizable liquid crystal composition, polarized light-emitting coating material, novel naphtholactam derivative, novel coumarin derivative, novel nile red derivative, and novel anthracene derivative
  • Polymerizable liquid crystal composition, polarized light-emitting coating material, novel naphtholactam derivative, novel coumarin derivative, novel nile red derivative, and novel anthracene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-1

[0386] [Example 1-1] Synthesis of Compound B-33

[0387] Compound B-33 was synthesized according to the method shown below.

[0388] That is, methanesulfonyl chloride (0.14 g, 0.0012 mol) and tetrahydrofuran (THF) (4.29 g) were added to the three-necked flask, and it cooled to -30 degreeC under nitrogen atmosphere. To this reaction solution, a THF (4.29 g) suspension of Intermediate 1 (300 mg, 0.001 mol) and triethylamine (TEA) (0.12 g, 0.012 mol) represented by the following [Chemical Formula 71] was added dropwise. After stirring for 3 hours, TEA (0.12 g, 0.0012 mol) and butyl acrylate (0.14 g, 0.001 mol) were added, returned to normal temperature, and stirred overnight. Chloroform and water were added to separate oil from water until it became neutral, the organic solvent was distilled off, and after separation by silica gel column chromatography (developing solvent: chloroform), crystallization was carried out from methanol to obtain 0.06 g of the target compound B- 33 (...

Embodiment 1-2

[0392] [Example 1-2] Synthesis of compound B-35

[0393] Compound B-35 was synthesized according to the method shown below.

[0394] That is, methanesulfonyl chloride (0.34 g, 0.003 mol) and THF (6.18 g) were added to the three-necked flask, and it cooled to -30 degreeC under nitrogen atmosphere. A THF (6.18 g) solution of Intermediate 2 (0.73 g, 0.0025 mol) and TEA (0.03 g, 0.003 mol) represented by the following [Chemical Formula 72] was added dropwise to the reaction solution. Further, a THF (6.18 g) solution of TEA (0.03 g, 0.003 mol) and N,N-dimethylaminopyridine (DMAP) (0.003 g) was added, and then intermediate 3 ( 0.86g, 0.0025mol) of THF (6.18g) solution, returned to room temperature and stirred overnight. Chloroform and water were added for oil-water separation, the organic solvent was distilled off, and after separation by silica gel column chromatography (developing solvent: chloroform: n-hexane = 1:1), crystallization was carried out from methanol to obtain 0.48 ...

Embodiment 1-3～1-9

[0401] [Examples 1-3 to 1-9] Synthesis of compounds B-169 to B-175

[0402] Compound B-169 was synthesized according to the method shown below.

[0403]

[0404] Add salicylaldehyde (2.93g, 0.024mol), benzyloxyphenylacetic acid (4.85g, 0.02mol), sodium acetate (3.28g, 0.040mol) and acetic anhydride (26.27g) in a 300ml four-necked flask. Heat at 130°C for 5 hours. It was added dropwise in aqueous sodium hydroxide solution, and the obtained white precipitate was filtered, washed by refluxing with methanol, and then the white solid was filtered to obtain 2.4 g of Intermediate 4 shown in the following [Chemical Formula 74] (yield: 36.5%) ).

[0405] [chemical formula 74]

[0406]

[0407]

[0408] In a 300ml four-neck flask, add intermediate 4 (2.17g, 0.066mol) and anisole (9.43g) obtained in step 1, and dropwise add an anisole solution that is dissolved with aluminum chloride (0.44g, 0.033mol) ( 1.57 g), heated at 85°C for 1 hour. Chloroform and water were added, the ...

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Abstract

The present invention provides a polymerizable liquid crystal composition that demonstrates favorable polarized light emission for a polarized light element, the composition using a polymerizable liquid crystal compound and colorant; also provided are a coating material, a medium, and a polarized light-element. Furthermore the present invention provides a favorable novel naphtholactam derivative, novel coumarin derivative, novel Nile red derivative, and novel anthracene derivative as the colorant. Specifically, provided is a polymerizable liquid crystal composition containing (A) at least one type of liquid crystal compound having a polymerizable functional group, (B) at least one type of colorant, and (C) a polymerization initiator; further provided are a novel naphthyl and derivative expressed by general formula (IV'), a novel coumarin derivative expressed by general formula (VI'), a novel Nile red derivative expressed by general formula (VII'), or a novel anthracene derivative expressed by general formula (VIII'), which are favorable as the colorant of component (B).

Description

technical field [0001] The present invention relates to a polymerizable liquid crystal composition containing a liquid crystal compound having a polymerizable functional group, a colorant, and a polymerization initiator, a polarized luminescent paint formed from the polymerizable liquid crystal composition, and a polarized luminescent paint formed by coating the polarized luminescent paint on a support. A laminate showing polarized luminescence obtained by coating and a polarizing element using the laminate. [0002] In addition, the present invention relates to novel naphthalactam derivatives, novel coumarin derivatives, novel Nile red derivatives, and novel anthracene derivatives suitable as the above-mentioned colorants. Background technique [0003] A liquid crystal composition (hereinafter referred to as a "polymerizable liquid crystal composition") containing at least one liquid crystal compound having a polymerizable functional group (hereinafter referred to as a "pol...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K19/38C09D4/00C09D5/22C09D201/02C09K19/60G02B5/30H01L51/50
CPCC09B57/06C09K19/54G02B5/3025C09K19/32H01L51/5293C08F220/30C09K19/3483C09K19/60C09K2019/0448C09K19/3486C09B57/02C09B69/101C09B69/109C08G59/00C08L63/00C07D265/34C07D265/36C07D265/38C07D311/06C08F220/303H10K50/13H10K50/868
Inventor 久保田裕介入泽正福矢野亨松本健
Owner ADEKA CORP
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