CN110483434A - 含炔键的大双折射率侧氟苯并噁唑液晶化合物及其制备方法 - Google Patents
含炔键的大双折射率侧氟苯并噁唑液晶化合物及其制备方法 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3483—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring
- C09K19/3486—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring the heterocyclic ring containing nitrogen and oxygen atoms
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明公开了一种含炔键的大双折射率侧氟苯并噁唑液晶化合物及其制备方法,属于材料技术领域。该化合物的结构式为式中R代表C2~C10的直链烷基,M代表氢、甲基或硝基。该化合物是以2‑氟‑4‑溴苯甲醛、2‑甲基‑3‑丁炔‑2‑醇、1‑碘‑4‑(烷氧基)苯、氨基酚为原料,通过Sonogashira偶联、亲核加成、关环等反应制备而成。本发明化合物具有大的双折射率,宽的液晶相区间,且其制备方法步骤简单、收率高,可用于液晶光电器件中,以提高其响应速度。
Description
技术领域
本发明属于液晶材料技术领域,具体涉及一种含炔键的大双折射率侧氟苯并噁唑液晶化合物及其制备方法。
背景技术
液晶材料广泛应用于平板电脑、手机、笔记本电脑和高清电视等显示领域,以及光调制器、激光光束偏转、自适应光学等非显示领域。液晶光电器件具有驱动电压低、相位调制量大、重量轻、功耗低等优点。
液晶材料是液晶光电器件的关键核心材料,而液晶光电器件的性能优化主要是通过调控液晶材料的结构和组分来实现。近年来,快速响应是液晶光电器件一直追求的重要发展方向。为了提高液晶光电器件的响应速度,一方面可以采用低粘度的液晶化合物,液晶化合物的粘度与液晶器件的响应时间有直接关系,即液晶材料的粘度越低,液晶器件的响应时间越小、响应速度越快;另一方面可以降低液晶器件盒厚,液晶器件盒厚越低,响应速度越快,而使用大双折射率(Δn)液晶材料能够在实际应用中有效减小液晶器件盒厚。因而大Δn液晶是液晶光电器件实现快速响应的关键材料。
液晶化合物结构一般由苯环、环己基、芳杂环等作为刚性骨架构建,可以通过引入炔键、增加苯环、引入氰基或异硫氰基等增加液晶分子共轭长度,进而提升液晶化合物的Δn。目前虽然有不少光学各向异性液晶材料,但是其Δn不够大、种类不够多,限制了其在液晶光电器件中的应用。尤其可作为液晶光电器件使用的大Δn芳杂环类液晶化合物种类非常少。
发明内容
本发明的目的是提供一种含炔键的大双折射率侧氟苯并噁唑液晶化合物,并为该化合物提供一种工艺步骤简单、收率高的制备方法。
针对上述目的,本发明所采用的含炔键的大双折射率侧氟苯并噁唑液晶化合物的结构式如下:
式中R代表C2~C10的直链烷基,M代表H、CH3、NO2中任意一种。
上述含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法由下述步骤组成:
1、制备4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇
将2-氟-4-溴苯甲醛、对甲苯磺酸、乙二醇加入三氯甲烷中,在50~70℃反应6~8h,减压蒸除溶剂,然后在氮气保护下,加入2-甲基-3-丁炔-2-醇、碘化亚铜、三苯基膦、四(三苯基膦)钯、三乙胺,在80~90℃下反应8~10h,分离纯化,得到4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇,反应方程式如下:
2、制备2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环
将4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇、式I所示1-碘-4-(烷氧基)苯、氢氧化钠、乙二醇乙醚和四(三苯基膦)钯加入甲苯中,在氮气保护下60~80℃反应8~10h,反应结束后,分离纯化,得到2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环,反应方程式如下:
式I中,R代表C2~C10的直链烷基。
3、制备2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛
将2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环、甲酸加入四氢呋喃中,在50~70℃下反应5~6h,反应结束后,分离纯化,得到2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛,反应方程式如下:
4、制备2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚
将2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛、式II所示氨基酚加入乙醇中,搅拌回流4~6h,减压蒸馏除去溶剂,重结晶得到2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚,反应方程式如下:
式II中,M代表H、CH3、NO2中任意一种。
5、制备含炔键的大双折射率侧氟苯并噁唑液晶
将2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚、二氯二氰基苯醌(DDQ)加入三氯甲烷中,回流反应4~6h后,停止反应,分离纯化,得到含炔键的大双折射率侧氟苯并噁唑液晶,反应方程式如下:
上述步骤1中,优选2-氟-4-溴苯甲醛与对甲苯磺酸、乙二醇的摩尔比4:0.8~1.2:85~95,2-氟-4-溴苯甲醛与2-甲基-3-丁炔-2-醇、碘化亚铜、三苯基膦、四(三苯基膦)钯的摩尔比1:1~1.2:0.04~0.06:0.08~0.12:0.015~0.025。
上述步骤2中,优选2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环与1-碘-4-(烷氧基)苯、氢氧化钠、乙二醇乙醚、四(三苯基膦)钯的摩尔比1:1~1.2:5.5~6.5:9.5~10.5:0.015~0.025。
上述步骤3中,优选2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环与甲酸的摩尔比为1:150~160。
上述步骤4中,优选2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛与氨基酚的摩尔比1:1.1~1.5。
上述步骤5中,优选2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚与二氯二氰基苯醌的摩尔比为1:1.1~1.5。
本发明的有益效果如下:
本发明液晶化合物是以2-氟-4-溴苯甲醛、2-甲基-3-丁炔-2-醇、1-碘-4-(烷氧基)苯、氨基酚为原料,通过Sonogashira偶联、亲核加成、关环等反应制备而成,其既具有杂环液晶介晶相类型,又具有较大的双折射率,同时具有宽的向列相区间,且其制备方法步骤简单、收率高,可用于液晶光电器件中,以提高其响应速度。
附图说明
图1是实施例1得到的液晶化合物的DSC曲线(升降温速率5℃/min)。
图2是实施例1得到的液晶化合物升温至164.0℃时的POM照片(200×)。
图3是实施例1得到的液晶化合物降温至163.8℃时的POM照片(200×)。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明,但本发明的保护范围不仅限于这些实施例。
实施例1
1、制备4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇
在装有冷凝管和搅拌子的250mL三口烧瓶中加入2-氟-4-溴苯甲醛5g(24.6mmol)、对甲苯磺酸1.06g(6.2mmol)、乙二醇34.62g(554.2mmol),并向其中加入经过分子筛干燥的三氯甲烷50mL,在60℃恒温油浴锅中搅拌6h后停止反应,减压蒸除溶剂,再向其中加入2-甲基-3-丁炔-2-醇1.87g(22.3mmol)、碘化亚铜0.19g(1.0mmol)、三苯基膦0.53g(2.0mmol),并加入80mL三乙胺作为反应溶剂,在80℃恒温油浴锅中加热并通氮气保护,反应1h后,在氮气保护下迅速加入四(三苯基膦)钯0.46g(0.4mmol),继续反应8h后停止反应。反应结束后,用水稀释反应体系,用二氯甲烷萃取,分出有机相,并用二氯甲烷重复萃取水相,合并有机相,将得到的有机相用饱和氯化铵水溶液洗涤三次,无水硫酸镁干燥,减压蒸馏旋出溶剂,向其中加入7g硅胶制样,柱色谱分离(洗脱剂为石油醚与乙酸乙酯体积比为30:1的混合液),得到黄色油状液体4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇4.6g,收率74.6%,反应方程式如下:
2、制备2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)-1,3-二氧戊环
在装有搅拌子和冷凝管的250mL单口瓶中依次加入4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇2.4g(9.6mmol)、1-碘-4-(戊氧基)苯3.0g(10.5mmol)、氢氧化钠2.3g(57.3mmol)、乙二醇乙醚8.6g(95.9mmol)和甲苯50mL,在70℃恒温油浴锅中加热并通氮气保护,反应1h后,在氮气保护下迅速加入四(三苯基膦)钯0.2g(0.19mmol),继续反应8h后停止反应。反应结束后,用水稀释反应体系,用二氯甲烷萃取,分出有机相,并用二氯甲烷重复萃取水相,合并有机相,将得到的有机相用饱和氯化铵水溶液洗涤三次,无水硫酸镁干燥,减压蒸馏旋出溶剂,向其中加入7g硅胶制样,柱色谱分离(洗脱剂为石油醚与乙酸乙酯体积比为50:1的混合液),得到淡黄色固体2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)-1,3-二氧戊环2.3g,收率67.7%,反应方程式如下:
3、制备2-氟-4-((4-(戊氧基)苯基)乙炔基)苯甲醛
在装有搅拌子和冷凝管的250mL单口烧瓶中依次加入2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)-1,3-二氧戊环2.2g(6.2mmol)、甲酸43.4g(0.94mol)、四氢呋喃80mL,在60℃恒温油浴中加热反应6h。反应结束后,用二氯甲烷和水萃取反应液,旋蒸浓缩,得到白色固体,加无水乙醇重结晶,得到白色固体2-氟-4-((4-(戊氧基)苯基)乙炔基)苯甲醛1.5g,收率77.9%,反应方程式如下:
4、制备2-((2-氟-4-((4-(戊氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚
在装有搅拌子和冷凝管的100mL单口瓶中加入2-氟-4-((4-(戊氧基)苯基)乙炔基)苯甲醛0.4g(1.3mmol)、邻氨基苯酚0.17g(1.5mmol)、无水乙醇40mL,80℃搅拌回流6h至反应完全。冷却到室温,有黄色针状晶体析出,用布氏漏斗抽滤,得到黄色固体2-((2-氟-4-((4-(戊氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚0.34g,收率65.7%,反应方程式如下:
5、制备2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)苯并噁唑液晶
在装有搅拌子和冷凝管的100mL单口瓶中加入2-((2-氟-4-((4-(戊氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚0.2g(0.5mmol)、二氯二氰基苯醌(DDQ)0.13g(0.58mmol)、三氯甲烷40mL,采用恒温油浴将其加热至回流,反应5h至反应完全。待反应液冷却到室温时,用二氯甲烷和水萃取反应液,合并有机相,旋除溶剂,加入2g硅胶制样,柱色谱分离(洗脱剂为石油醚与乙酸乙酯体积比为4:1的混合液),得到白色固体2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)苯并噁唑液晶0.19g,收率95.5%,反应方程式如下:
产物的波谱数据如下:
IR(KBr)v(cm-1):2928,2849,2209,1600,1506,1564,1248,1116,830,740.
1H-NMR(400MHz,CDCl3,TMS)δ(ppm)=8.19(t,J3 H-H=8.0Hz,1H),7.97-7.72(m,1H),7.70-7.53(m,1H),7.50-7.44(m,2H),7.44-7.32(m,4H),7.03-6.76(m,2H),4.14-3.67(t,J3 H-H=6.4Hz,2H),1.99-1.63(m,2H),1.53-1.16(m,4H),0.92(t,J3 H-H=7.2Hz,3H).
MS(MALDI-TOF)m/z:理论值399.47,实测值399.19.
实施例2
本实施例的步骤4中,用等摩尔2-氨基-4-甲基苯酚替换实施例1步骤4中的邻氨基苯酚,其他步骤与实施例1相同,得到结构式如下的2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)-5-甲基苯并噁唑,收率94.2%,结构式如下:
产物的波谱数据如下:
IR(KBr)v(cm-1):2944,2857,2009,1608,1507,1247,1116,1029,830,795.
1H-NMR(400MHz,CDCl3,TMS)δ(ppm)=8.17(t,J3 H-H=8.0Hz,1H),7.59(m,1H),7.49-7.43(m,3H),7.38(m,2H),7.18(m,1H),6.91-6.84(m,2H),3.96(t,J3 H-H=6.6Hz,2H),2.48(s,3H),1.79(m,2H),1.49-1.31(m,4H),0.93(t,J3 H-H=7.1Hz,3H).
MS(MALDI-TOF)m/z:理论值413.49,实测值413.19.
实施例3
本实施例的步骤4中,用等摩尔2-氨基-4-硝基苯酚替换实施例1步骤4中的邻氨基苯酚,其他步骤与实施例1相同,得到结构式如下的2-(2-氟-4-((4-(戊氧基)苯基)乙炔基)苯基)-5-硝基苯并噁唑,收率75.3%,结构式如下:
产物的波谱数据如下:
IR(KBr)v(cm-1):2939,2873,2196,1606,1514,1248,1123,1006,830,732.
1H-NMR(400MHz,CDCl3,TMS)δ(ppm)=8.69(d,J4 H-H=2.2Hz,1H),8.34(m,1H),8.19(t,J3 H-H=8.0Hz,1H),7.70(d,J2 H-H=9.2Hz,1H),7.59-7.30(m,4H),7.00-6.74(m,2H),3.97(t,J=6.6Hz,2H),1.97-1.66(m,2H),1.51-1.25(m,4H),0.93(t,JH-H=7.1Hz,3H).
MS(MALDI-TOF)m/z:理论值444.46,实测值443.26.
实施例4
本实施例的步骤2中,用等摩尔1-碘-4-(乙氧基)苯替换实施例1步骤2中的1-碘-4-(戊氧基)苯,其他步骤与实施例1相同,得到结构式如下的2-(2-氟-4-((4-(乙氧基)苯基)乙炔基)苯基)苯并噁唑,收率93.1%,结构式如下:
产物的波谱数据如下:
IR(KBr)v(cm-1):2966,2911,2873,2192,1607,1576,1489,1419,1247,1106,1028,802,755.
1H-NMR(400MHz,)δ8.20(t,J3 H-H=8.0Hz,1H),7.87-7.78(m,1H),7.65-7.57(m,1H),7.50-7.47(J3 H-H=2.8Hz,1H),7.47-7.45(q,J3 H-H=2.8Hz,1H),7.44-7.33(m,4H),6.91-6.88(t,J3 H-H=2.8Hz,1H),6.88-6.86(t,J3 H-H=2.8Hz,1H),4.06(q,J4 H-H=7.2Hz,2H),1.43(t,J3 H-H=7.2Hz,3H).
MS(MALDI-TOF)m/z:理论值357.38,实测值357.19.
实施例5
本实施例的步骤2中,用等摩尔1-碘-4-(丙氧基)苯替换实施例1步骤2中的1-碘-4-(戊氧基)苯,其他步骤与实施例1相同,得到结构式如下的2-(2-氟-4-((4-(丙氧基)苯基)乙炔基)苯基)苯并噁唑,收率91.9%,结构式如下:
产物的波谱数据如下:
IR(KBr)v(cm-1):2966,2880,2200,1591,1560,1511,1417,1240,1028,849,739.
1H-NMR(400MHz,CDCl3,TMS)δ(ppm)=8.0(t,J3 H-H=7.9Hz,1H),7.86-7.79(m,1H),7.64-7.57(m,1H),7.49-7.47(J3 H-H=2.8Hz,1H),7.47-7.45(J3 H-H=2.8Hz,1H),7.44-7.36(m,4H),6.92-6.88((t,J3 H-H=2.8Hz,1H),6.88-6.86((t,J3 H-H=2.4Hz,1H),3.94(t,J3 H-H=6.4Hz,2H),1.88-1.76(m,2H),1.09-1.00(t,J3 H-H=7.6Hz,3H).
MS(MALDI-TOF)m/z:理论值371.41,实测值371.13.
对上述实施例1~5制备的液晶化合物的光学各向异性和热性能进行测试,得到其双折射率、相转变温度和相变焓。双折射率可通过Gaussian09软件理论计算得到理论值,也可通过阿贝折光仪测试得到实验值。相转变温度和相变焓可通过差示扫描量热仪(DSC)得到。结果见表1和表2。
表1双折射率
表2相转变温度和相变焓
注:表中Cr代表结晶相;N代表向列相;I代表各向同性。
由表1可见,本发明液晶化合物(实验值Δn≥0.511)与文献(Liquid Crystals,2017,44:14-15,2184-2191)中的大双折射率液晶化合物(测试值Δn=0.305)相比,Δn显著提高,进一步证明本发明液晶化合物具有优异的光学各向异性。
由表2可见,本发明液晶化合物具有较宽的向列相温度区间。
由图1的DSC曲线(升降温速率5℃/min)及图2和3的POM照片(200×)可见,本发明化合物具有向列相的液晶织构及在升降温中均具有液晶相态。
Claims (7)
1.一种含炔键的大双折射率侧氟苯并噁唑液晶化合物,其特征在于该化合物的结构式如下:
式中R代表C2~C10的直链烷基,M代表H、CH3、NO2中任意一种。
2.一种权利要求1所述的含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法,其特征在于它由下述步骤组成:
(1)制备4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇
将2-氟-4-溴苯甲醛、对甲苯磺酸、乙二醇加入三氯甲烷中,在50~70℃反应6~8h,减压蒸除溶剂,然后在氮气保护下,加入2-甲基-3-丁炔-2-醇、碘化亚铜、三苯基膦、四(三苯基膦)钯、三乙胺,在80~90℃下反应8~10h,分离纯化,得到4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇,反应方程式如下:
(2)制备2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环
将4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇、式I所示1-碘-4-(烷氧基)苯、氢氧化钠、乙二醇乙醚和四(三苯基膦)钯加入甲苯中,在氮气保护下60~80℃反应8~10h,反应结束后,分离纯化,得到2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环,反应方程式如下:
式I中,R代表C2~C10的直链烷基;
(3)制备2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛
将2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环、甲酸加入四氢呋喃中,在50~70℃下反应5~6h,反应结束后,分离纯化,得到2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛,反应方程式如下:
(4)制备2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚
将2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛、式II所示氨基酚加入乙醇中,搅拌回流4~6h,减压蒸馏除去溶剂,重结晶得到2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚,反应方程式如下:
式II中,M代表H、CH3、NO2中任意一种;
(5)制备含炔键的大双折射率侧氟苯并噁唑液晶
将2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚、二氯二氰基苯醌加入三氯甲烷中,回流反应4~6h后,停止反应,分离纯化,得到含炔键的大双折射率侧氟苯并噁唑液晶。
3.根据权利要求2所述的含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法,其特征在于:步骤(1)中,所述2-氟-4-溴苯甲醛与对甲苯磺酸、乙二醇的摩尔比4:0.8~1.2:85~95,2-氟-4-溴苯甲醛与2-甲基-3-丁炔-2-醇、碘化亚铜、三苯基膦、四(三苯基膦)钯的摩尔比1:1~1.2:0.04~0.06:0.08~0.12:0.015~0.025。
4.根据权利要求2所述的含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法,其特征在于:步骤(2)中,所述4-(4-(1,3-二氧戊环-2-基)-2-氟苯基)-2-甲基丁-3-炔-2-醇与1-碘-4-(烷氧基)苯、氢氧化钠、乙二醇乙醚、四(三苯基膦)钯的摩尔比1:1~1.2:5.5~6.5:9.5~10.5:0.015~0.025。
5.根据权利要求2所述的含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法,其特征在于:步骤(3)中,所述2-(2-氟-4-((4-(烷氧基)苯基)乙炔基)苯基)-1,3-二氧戊环与甲酸的摩尔比为1:150~160。
6.根据权利要求2所述的含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法,其特征在于:步骤(4)中,所述2-氟-4-((4-(烷氧基)苯基)乙炔基)苯甲醛与氨基酚的摩尔比1:1.1~1.5。
7.根据权利要求2所述的含炔键的大双折射率侧氟苯并噁唑液晶化合物的制备方法,其特征在于:步骤(5)中,所述2-((2-氟-4-((4-(烷氧基)苯基)乙炔基)苯亚甲基)氨基)苯酚与二氯二氰基苯醌的摩尔比为1:1.1~1.5。
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