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Polymerizable compound based on dibenzofuran and preparation method and application thereof

A technology of polymer compounds and polymer compositions, applied in the field of optical materials, can solve the problems of poor film non-uniformity, easy precipitation, and difficulty in stable storage.

Pending Publication Date: 2022-03-08
江苏创拓新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing polymerizable compounds are not easy to store stably in this situation, and are easy to precipitate
In the case of insufficient maximum stable concentration, an undesirable consequence is that the non-uniformity of the film becomes worse

Method used

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  • Polymerizable compound based on dibenzofuran and preparation method and application thereof
  • Polymerizable compound based on dibenzofuran and preparation method and application thereof
  • Polymerizable compound based on dibenzofuran and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0081] Synthesis of Intermediate 1:

[0082]

[0083] 4-Hydroxybutyl acrylate, dichloromethane, pyridine, dichloromethane solution with triphosgene added dropwise, keep warm for 1 hour after the dropwise addition, add water dropwise, separate liquids, collect the lower layer, concentrate to dry dichloromethane to obtain intermediate 1 for later use .

[0084]

[0085] Synthesis of Compound A:

[0086]

[0087] Add 10g of 3,7-dihydroxydibenzofuran, 31.3g of intermediate 1, and 100g of dichloromethane into the reaction flask, then add 23g of diisopropylethylamine dropwise at a controlled temperature of 0-5°C, and add In water, separated and washed once with water, dried and concentrated, crystallized in a mixed solvent of toluene and ethanol, the compound B after drying was 21.4g, content: 97.6%, yield: 78.7%. 1 H NMR (400MHz, DMSO-d 6 ): δ7.88(d,2H.),7.84(s,2H.),7.27(d,2H.),6.29(d,2H.),6.05(t,2H.),5.61(d,2H. ), 4.24(t, 4H.), , 3.98(t, 4H.), 1.63(m, 8H.).

Synthetic example 2

[0088] Synthesis Example 2: Synthesis of Compound B

[0089]

[0090] Synthesis of Compound B:

[0091]

[0092] Add 10g of 3,7-dihydroxy-4-fluorodibenzofuran, 31.3g of intermediate 1, and 100g of dichloromethane into the reaction flask, and then add 23g of diisopropylethylamine dropwise at a controlled temperature of 0-5°C. After the reaction is complete, add water, wash once with water, dry and concentrate, crystallize in a mixed solvent of toluene and ethanol, and dry compound B21.4g, content: 97.6%, yield: 78.7% 1 H NMR (400MHz, DMSO-d 6 ): δ7.88(d,1H.),7.84(s,1H.),7.63(d,1H.),7.27(d,1H.),7.25(d,1H.),6.29(d,2H. ), 6.05(t, 2H.), 5.61(d, 2H.), 4.24(t, 4H.), 3.98(t, 4H.), 1.63(m, 8H.).

Synthetic example 3

[0093] Synthesis Example 3: Synthesis of Compound C

[0094]

[0095] Add 10g of 3,7-dihydroxy-4,8-difluorodibenzofuran, 27.4g of intermediate 1 of Synthesis Example 2, and 100g of dichloromethane into the reaction flask, and then add dichloromethane dropwise at a temperature of 0-5°C. 20.5 g of isopropylethylamine was added into water after the reaction was complete, separated and washed once with water, dried and concentrated, crystallized in a mixed solvent of toluene and ethanol, and the compound C after drying was 20.7 g, content: 98.1%, yield: 82.7%. 1 H NMR (400MHz, DMSO-d 6 ):7.64(s,2H.),7.27(d,2H.),6.29(d,2H.),6.05(t,2H.),5.61(d,2H.),4.24(t,4H.), , 3.98 (t, 4H.), 1.63 (m, 8H.).

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Abstract

The invention discloses a polymerizable compound based on dibenzofuran and a preparation method and application thereof, the compound is selected from compounds of a general formula (1), and P1, P2, L1, L2, R1 and R2 are as described in the context. The polymerizable compound is capable of exhibiting one or more of favorable substrate high adhesion in an RM optical retardation film, high transparency to Vis-light, exhibiting reduced random yellowing, and exhibiting good high temperature stability, and the like.

Description

technical field [0001] The invention relates to a dibenzofuran-based polymerizable compound and its preparation method and application, in particular to the application of the polymerizable compound in various optical anisotropic bodies; it belongs to the technical field of optical materials. Background technique [0002] Polymerizable (mesogenic) compounds (RMs) as raw materials for the preparation of various optically anisotropic bodies are attracting more and more attention. The prior art usually coats a solution of a polymerizable compound onto a substrate, aligns it, and cures it by heating or irradiating active energy rays to form an optically anisotropic polymer film with a uniform orientation, also known as an optically anisotropic polymer film. Anisotropic body. The orientation of the film can be along the plane (the liquid crystal molecules are aligned substantially parallel to the layer), homeotropic (rectangular or perpendicular to the layer) or oblique, and can...

Claims

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Application Information

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IPC IPC(8): C07D307/91C09K19/38C08F222/20G02B1/08
CPCC07D307/91C09K19/3861C08F222/1025G02B1/08C08F222/1035
Inventor 叶永殷勇谭玉东靳灿辉
Owner 江苏创拓新材料有限公司
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