Optical film, image display device, diethynylfluorene, and polymer thereof
a technology of diethynylfluorene and optical film, applied in the direction of optical elements, polarising elements, instruments, etc., can solve the problems of comparatively thick and heavy liquid crystal display having this optical film, and achieve excellent viewing angle properties, thin and lighter weight, and high rigidity and linearity of the main chain
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synthesis example 1
Synthesis of 2,7-dihydroxy-9,9-[2,7-bis(2-methyl-2-hydroxy-3-butynyl)fluorenyl]xanthene
[0155]30.0 g of 2,7-dibromofluorenone and 24.43 g of resorcinol were dissolved in 100 mL of toluene, and 3.48 g of concentrated sulfuric acid and 0.09 g of mercaptopropionic acid were added thereto and the mixture was heated at 80° C. for 18 hours. After completion of the reaction, the solution was neutralized with sodium hydroxide and chloroform was added thereto, and the precipitated solid was separated by filtration to thereby obtain a bromo derivative.
[0156]Next, 0.008 g of bis(triphenylphosphine)dichloropalladium (II) and 0.002 g of copper iodide (I) were dissolved in 1.0 mL of dioxane under a nitrogen atmosphere. 0.005 g of tri(tertiary butyl)phosphine, 0.046 g of di-isopropylamine, 0.037 g of 2-methyl-3-butyne-2-ol, and 0.10 g of the obtained bromo derivative were added to the solution, and the solution was stirred at 80° C. for 24 hours. Thereafter, the solvent was removed under reduced pr...
synthesis example 2
Synthesis of 2,7-dihydroxy-9,9-[2,7-bis(5-hexynyl)fluorenyl]xanthene
[0158]1.010 g of palladium carbon and 0.365 g of copper iodide (I) were dissolved in 95 mL of dimethylacetamide and 5 mL of water under a nitrogen atmosphere. 0.800 g of triphenylphosphine, 0.046 g of di-isopropylamine, 4.000 g of 1-hexyne, and 10.00 g of the bromo derivative obtained in the above-mentioned were added to the solution, and the solution was stirred at 80° C. for 24 hours. Thereafter, the solvent was removed under reduced pressure and the residue was purified in a silica gel packed column with the use of a developing solvent (a mixed solvent of hexane and ethyl acetate). After the purification, 3.370 g of a compound (yield 33.8%) was obtained. Through the measurement by NMR, the obtained compound was 2,7-dihydroxy-9,9-[2,7-bis(5-hexynyl)fluorenyl]xanthene represented by the following formula (2).
[0159]
example 1
[0160]4 mL of pyridine was added to 0.52 g of ice-cooled thionyl chloride. 0.17 g of isophthalic acid and 0.17 g of terephthalic acid were dissolved in 4 mL of pyridine, and this solution was slowly added to the above-mentioned pyridine containing the above-mentioned thionyl chloride over 5 to 10 minutes. Thereafter, the cooling bath was removed and the solution was stirred at room temperature for 20 minutes (this mixed solution is called Solution A). On the other hand, 0.34 g of bis(4-hydroxyphenyl)hexafluoropropane and 0.52 g of 2,7-dihydroxy-9,9-[2,7-bis(5-hexynyl)fluorenyl]xanthene obtained in the above-mentioned were dissolved in 4 mL of a pyridine solution (this solution is called Solution B). Solution B was added to Solution A at a time, and the mixture was heated at 80° C. for 4 hours and thereafter stirred for one night. The obtained solution was diluted with chloroform and thereafter poured into methanol. The precipitated polymer was refluxed in methanol, filtered off and...
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