CN118085884A - 含2,3-二氟取代苯的异硫氰酸酯液晶化合物及液晶组合物 - Google Patents
含2,3-二氟取代苯的异硫氰酸酯液晶化合物及液晶组合物 Download PDFInfo
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- CN118085884A CN118085884A CN202211512587.5A CN202211512587A CN118085884A CN 118085884 A CN118085884 A CN 118085884A CN 202211512587 A CN202211512587 A CN 202211512587A CN 118085884 A CN118085884 A CN 118085884A
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- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- VCAFHMCSPWVSJS-UHFFFAOYSA-N 1-butyl-4-(4-ethynylphenyl)benzene Chemical group C1=CC(CCCC)=CC=C1C1=CC=C(C#C)C=C1 VCAFHMCSPWVSJS-UHFFFAOYSA-N 0.000 description 1
- HLUVLSYQSNGSKG-UHFFFAOYSA-N 1-ethynyl-4-(4-propylcyclohexyl)benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C#C)C=C1 HLUVLSYQSNGSKG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
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- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
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- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
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- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01Q—ANTENNAS, i.e. RADIO AERIALS
- H01Q21/00—Antenna arrays or systems
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01Q—ANTENNAS, i.e. RADIO AERIALS
- H01Q3/00—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system
- H01Q3/26—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system varying the relative phase or relative amplitude of energisation between two or more active radiating elements; varying the distribution of energy across a radiating aperture
- H01Q3/30—Arrangements for changing or varying the orientation or the shape of the directional pattern of the waves radiated from an antenna or antenna system varying the relative phase or relative amplitude of energisation between two or more active radiating elements; varying the distribution of energy across a radiating aperture varying the relative phase between the radiating elements of an array
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
- C09K2019/183—Ph-Ph-C≡C-Ph
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- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
- C09K2019/3063—Cy-Ph-C≡C-Ph
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Abstract
本发明公开了一种包含侧向2,3‑二氟取代苯的异硫氰酸酯液晶化合物及液晶组合物。所公开化合物的结构通式如Ⅰ所示,其中R为碳原子数为1~10的烷基或烷氧基、碳原子数为2‑10的烯基或烯氧基、碳原子数为3‑8的环烷基或含环烷基取代的烷基,其中碳原子上的氢可以被氟取代;Z1、Z2为单键、‑C≡C‑、‑CH=CH‑、‑CF=CF‑、‑CH2CH2;环A、环B为苯环或环己烷、环己烯,其中苯环上的氢可以被氟、氯、甲基、乙基取代;n=0,1,2。本发明液晶化合物具有宽向列相温度区间、低粘度、高双折射率的优点。
Description
技术领域
本发明属于液晶材料技术领域,具体涉及一种含有2,3-二氟苯异硫氰酸酯液晶化合物及其合成方法和液晶组合物。
背景技术
液晶材料在光电显示器件中得到了广泛应用,例如在各种液晶电视、桌面液晶显示器、移动显示终端等。近年来,随着微波及太赫兹通讯、光通信、激光相控阵等技术的不断发展,对具有高双折射率、低粘度、宽温区的液晶材料提出迫切需求。例如,在微波(1-100GHz)波段,液晶的双折射率(Δn)越高,其介电各项异性值也越大;在光通信、激光相控阵等液晶器件中,对于同样的光学相位调制量,双折射率(Δn)越高的液晶其对应的液晶光学元件厚度越小,响应时间大幅度缩短。
对于面向低轨卫星通信的微波组件如微波相控阵天线,以及液晶光学器件,响应时间也是关键指标之一。液晶的粘度与响应时间成正比,因此,为进一步提升器件的响应速度(即缩短响应时间),迫切需要开发具有低粘度特性的液晶材料。
此外,对于相控阵天线等户外应用的器件,还需要液晶具备宽温区特性。
高双折射率液晶分子中必须具有长共轭链结构,例如分子骨架采用联苯、三联苯、四联苯、二苯乙炔的长共轭结构,分子末端基采用氰基(-CN)或异硫氰酸酯基(-NCS)。尤其是含有异硫氰酸酯基(-NCS)的液晶分子,较含氰基(-CN)的分子具有更高的双折射率、更低的粘度、更高的电阻率等优点,成为研究开发及应用的重点。
含有异硫氰酸酯基(-NCS)的液晶,为改善其液晶相特性,例如获得具备向列相的特性,大都需要在分子引入氟原子。例如在苯环上异硫氰酸酯基的邻位引入1个或2个氟原子的液晶化合物,已经在下述文献中公开:
[1]Catanescu CO,Wu ST,Chien LC.Tailoring the physical properties ofsome high birefringence isothiocyanato-based liquid crystals.Liq Cryst.2004;31:541-555.
[2]Parish A,Gauza S,Wu S.T,Dziaduszek J,Dabrowski R.New fluorinatedterphenyl isothiocyanate liquid crystals.Liq Cryst.2008;35:79-86.
[3]Song Q,Gauza S,Xianyu H,Wu ST,Liao YM,Chang CY,Hsu C S.Highbirefringence lateral difluoro phenyl tolane liquid crystals.Liq Cryst.2010;37:139–147.
[4]R,Kula P,Herman J.High birefringence liquidcrystals.Crystals.2013;3(3):443-482.
对于液晶相位调制器等光学器件,以及用于微波通信的液晶天线,期望具备快速响应的能力。液晶的响应速度主要取决与液晶器件的盒厚(d)、液晶材料的旋转粘度(γ1)和弹性常数(K11),如下所示:
其中:ton为开态(加电)响应时间,toff为关态(撤电)响应时间;Vth为液晶的阈值电压,V为外加驱动电压;在盒厚d固定的情况下,要提升液晶器件的响应速度,必须要求液晶材料具备低旋转粘度(γ1)、大弹性常数(K11),即低的粘度弹性常数比值(γ1/K11)。
但现有的氟取代异硫氰酸酯基(-NCS)的高双折射率液晶,仍然存在向列液晶相温区范围窄、粘度相对较高、旋转粘度/弹性常数比值较高等问题。
为进一步满足光学、微波等元器件的工作性能要求,迫切需要研究开发双折射率更高、向列相温区宽、粘度低、旋转粘度/弹性常数比值低的新型液晶化合物及组合物。
发明内容
为了克服背景技术中存在的缺陷或不足,本发明提供一种新型具有2,3-二氟苯异硫氰酸酯类液晶化合物。
为了实现上述任务,本发明提供的化合物结构如通式Ⅰ所示:
其中:
R为碳原子数为1~10的烷基、氢被氟取代的烷基、烷氧基或氢被氟取代的烷氧基;或者为碳原子数为2-10的烯基、氢被氟取代的烯基、烯氧基或氢被氟取代的烯氧基;或者为碳原子数为3-8的环烷基、氢被氟取代的环烷基、含环烷基取代的烷基或氢被氟取代的含环烷基取代的烷基;
Z1为单键、-C≡C-、-CH=CH-、-CF=CF-或-CH2CH2;
Z2为单键、-C≡C-、-CH=CH-、-CF=CF-或-CH2CH2;
其中Z1和Z2至少有一个是选自-C≡C-、-CH=CH-、-CF=CF-或-CH2CH2;
环A为苯环、环己烷、环己烯或氢被氟、氯、甲基或/和乙基取代的苯环;n=0,1或2;
环B为苯环、环己烷、环己烯或氢被氟、氯、甲基或/和乙基取代的苯环。
进一步,n=0。
进一步,n=1,环A为苯环或环己烷。
进一步,n=2,环A为苯环或环己烷。
进一步,Z1和Z2至少有一个是-C≡C-。
进一步,所述化合物结构式为Ⅰ-1~Ⅰ-8式中任一结构式所示;
本发明还提供了上述化合物的合成方法。所提供的方法包括:
(1)2,3-二氟苯胺与卤化试剂反应,得到4-卤素取代-2,3-二氟苯胺;
(2)4-卤素取代-2,3-二氟苯胺在过渡金属催化下与芳基硼酸衍生物或含末端炔基的衍生物进行偶联反应,得到联苯胺类中间体或炔基苯胺类中间体;
(3)联苯胺类中间体或炔基苯胺类中间体进行光气化反应得到异硫氰酸酯类液晶化合物。
可选的,步骤(1)中卤化试剂选自碘、溴或N-溴代丁二酰亚胺。
可选的,所述的过渡金属催化剂选自含钯的配合物或镍的配合物。
本发明同时提供了一种液晶组合物。所提供的液晶组合物包含结构通式Ⅰ所示的一种或多种结构不同的液晶化合物。
优选的方案中,液晶组合物中包含一种或多种选自结构通式Ⅰ-1~Ⅰ-11所示的液晶化合物。
更优选的方案中,本发明液晶组合物中包含组分I-1所示的液晶化合物。具体方案中,组分I-1所示的液晶化合物质量百分比含量大于等于40%。
具体方案中,本发明所述的液晶组合物中结构通式Ⅰ所示的液晶化合物的质量百分比含量为10~100%。进一的方案中,本发明的液晶组合物还包含一种或多种选自结构通式Ⅱ所示的液晶化合物作为第二组分,其质量百分比含量为0~90%。
其中,R1为碳原子数为1~10的烷基、烷氧基、氟化烷基;或者为,碳原子数为2-10的烯基、烯氧基、氟化烯基、氟化烯氧基;或者为,碳原子数为3-8的环烷基或含环烷基取代的烷基;环C为苯环、环己烷或环己烯;m=0,1;n=0,1;X1,X2,X3为氢或氟。
进一步优选的方案中,结构通式Ⅱ选自以下Ⅱ-1~Ⅱ~12所示的液晶化合物:
进一步的方案中,本发明的液晶组合物还可包含0.001~1%的添加剂,所述添加剂选自受阻酚类抗氧化剂或/和受阻胺类光稳定剂等。其中受阻酚类抗氧化剂优选自以下结构:
其中R'为碳数1~9的烷基或烷氧基。
所述的受阻胺类光稳定剂优选自以下结构:
优选的受阻酚类抗氧化剂及受胺类光稳定剂在液晶组合物中的质量百分比添加量为0.01%~0.5%,更优选0.02%~0.2%。
还有些进一步的方案中,本发明液晶组合物还可包含一种或多种手性添加剂,含量为0.01%~1%;优选0.1%~0.5%。所述手性添加剂优选自以下结构:
其中R″为:碳原子数1~9的烷基或烷氧基。
根据本发明所述的液晶组合物,其双折射率大于0.30,进一步优选大于0.35;其旋转粘度小于200mPa·s,进一步优选小于180mPa·s;其旋转粘度/弹性常数比小于14,进一步优选小于12。
本发明所述的液晶化合物,尽管与现有技术公开的含侧向氟取代的异硫氰酸酯类液晶具有相类似的分子骨架,但是通过在苯环的2,3取代位点引入氟取代基后,与现有技术公开或已经应用的邻位单氟或者二氟取代的异硫氰酸酯类液晶相比,获得令人惊讶的结果:(1)显著改善的液晶相变温度特性,例如清亮点大幅增高、向列液晶相加宽;(2)包含2,3-二氟取代液晶化合物的液晶组合物,具有较高的清亮点和较宽的工作温区,极低的旋转粘度/弹性常数比值。综上所述,本发明所公开的含2,3-二氟取代苯的异硫氰酸酯类液晶化合物,突破了传统液晶化合物的认知水平。
本发明所述的液晶化合物和组合物可用于液晶光学器件,如工作在近红外波段的相位调制器、光学相控阵、波长选择开关等。本发明所述的液晶化合物和组合物还可用于液晶高频微波组件,例如全息液晶相控阵天线。
具体实施方式
除非有特殊说明,本文中的科学与技术术语及方法根据相关领域普通技术人员的认识理解或采用已有相关方法实现。
以下结合具体实施例对本发明做进一步详细说明。
需要说明的是,本发明涉及到的物理性能及光电性能详细测试方法如下:
(1)液晶相变温度:
采用示差扫描量热法(DSC):氮气气氛下,设置升温(降温)速率为5℃/min。
偏光热台法:将液晶样品置于正交偏光显微热台中,设置升温速率为2℃/min。在偏光显微镜中观察液晶相变的织构图像,确定液晶相态。
(2)双折射率(Δn):采用阿贝折光仪,25℃恒温条件下,光源589nm,分别测量寻常光(no)和非寻常光(ne)的折射率。
(3)介电常数(Δε,1KHz):25℃恒温条件下,将液晶灌入20μm反平行盒中,采用LCR表测试。Δε=ε∥-ε⊥,即分子长轴方向介电常数(ε∥)与分子短轴方向介电常数(ε⊥)的差值,外推得到介电各向异性值Δε。
(4)旋转粘度(γ1):25℃恒温条件下,将液晶灌入20μm反平行盒中,通过对液晶测试盒施加电压,测试液晶分子随电场运动偏转的瞬态电流值Ip,计算并外推得到旋转粘度γ1。
(5)弹性常数(K11,K33):25℃恒温条件下,通过测试液晶电容-电压(C-V)曲线,拟合得到K11和K33。
(6)高频下的介电常数及介电损耗(Δε,tanδ,19GHz):25℃恒温条件下,将液晶灌入聚四氟乙烯(PTFE)或熔融石英毛细管中,将填装有液晶的毛细管插入谐振腔室的中部。然后施加输入信号源,用矢量网络分析器来记录输出信号的结果。测量填装有液晶的毛细管与空白毛细管之间的共振频率与Q因子的变化,计算得到介电常数和损耗角正切值。垂直和平行于液晶指向矢的介电常数分量通过液晶在磁场中的取向来获得,相应地设置磁场的方向,并随后相应地旋转90°。
对于单体液晶,可以将其按照15:85的质量比例溶解到基础配方HOST中测试性能参数,再外推得到其性能参数。基础配方HOST是由以下三种单体液晶按照1:1:1的质量比例混合均匀得到。
本文相关代号和说明见下表1-3:
表1物理参数
代号 | 说明 | 单位 |
Tni | 清亮点 | ℃ |
LTS | 低温存储温度 | ℃ |
ε⊥ | 垂直于指向矢的介电常数 | |
ε∥ | 平行于指向矢的介电常数 | |
Δε | 介电各向异性 | |
tanδ⊥ | 垂直于指向矢的介电损耗正切 | |
tanδ∥ | 垂直于指向矢的介电损耗正切 | |
Δn | 双折射率 | |
γ1 | 旋转粘度 | mPa·s |
K11 | 展曲弹性常数 | pN |
K33 | 弯曲弹性常数 | pN |
τ | 介电调谐率 | |
η | 品质因子 |
表2本文结构单元缩写
表3结构缩写举例
液晶相变温度:C代表熔点,S代表近晶相,N代表向列相,I代表液态。
实施例1:
该实施例为2,3-二氟-1-异硫氰酸酯基-4-((4-正戊基苯基)乙炔基)苯的合成,具体方法如下:
(1)将12.9g 2,3-二氟苯胺、100mL二氯甲烷、8.4g碳酸氢钠加入反应容器中,室温搅拌,分批加入25.4g碘,搅拌反应过夜,分出有机层,用亚硫酸氢钠水溶性洗涤,再水洗至中性;浓缩除去溶剂,所得产物用石油醚重结晶,得到2,3-二氟-4-碘苯胺21g;
(2)氮气保护下,向反应器中加入12.8g 2,3-二氟-4-碘苯胺,三乙胺100mL,二三苯基膦氯化钯0.35g,碘化亚铜0.29g,三苯基膦0.39g,升温至50℃,滴加溶有8.6g 4-正戊基苯乙炔的30mL三乙胺溶液,滴完后保温反应4h,冷却至室温,过滤,滤液浓缩至干,加入100mL甲苯,水洗,干燥,减压除去甲苯,加入石油醚重结晶,得到棕色固体13.5g;
(3)将上步所得棕色固体10.0g、氯仿100mL、水25mL加入反应容器中,降温至5℃以下,缓慢滴加硫光气5.8g,滴加完后,升温至回流反应2h,降温至室温,分液,有机层用碳酸氢钠水溶液洗涤,再用水洗至中性,减压蒸馏除去溶剂,所得产物过硅胶柱,用正庚烷洗脱,产物用正庚烷重结晶,得到白色固体8.6g,气相色谱纯度99.9%。
上述方法合成路线如下所示:
所述产物结构鉴定数据如下:1H NMR(500MHz,CDCl3)δ(ppm):0.892(t,J=7Hz,3H),1.280~1.327(m,4H),1.589~1.649(m,2H),2.621(t,J=8Hz,2H),6.925(m,1H),7.181(d,J=9Hz,2H),7.203~7.224(m,1H),7.459(d,J=9Hz,2H).13C NMR(125MHz,CDCl3)δ(ppm):14.0,22.5,30.9,31.4,35.9,80.4,97.6,113.2(d,J=12.5Hz),119.2,120.8(d,J=4Hz),121.8(d,J=12Hz),127.6(d,J=4Hz),128.6,131.7,142.9,144.6,147.5(dd,J1=250Hz,J2=12.5Hz),151.1(dd,J1=250Hz,J2=12.5Hz).
MS m/z(RI,%):341.2(M+,70),284.1(100)。
DSC:C 52.7N 61.1I。
采用相同的合成方法,制备得到如表4所列化合物:
表4
实施例2:
该实施例为2,3-二氟-1-异硫氰酸酯基-4-((4-(4-正丙基环己基)苯基)乙炔基)苯的合成,具体方法如下:
用4-(4-正丙基环己基)苯乙炔替代实施例1中的4-正戊基苯乙炔,其他操作采用与实施例1同样的合成方法,得到2,5-二氟-1-异硫氰酸酯基-4-((4-(4-正丙基环己基)苯基)乙炔基)苯。
结构鉴定数据如下:1H NMR(500MHz,CDCl3)δ(ppm):0.900(t,3H,J=7.5Hz),0.999~1.442(m,9H),1.835~1.895(m,4H),2.447~2.485(m,1H),6.894(t,1H,J=8Hz),7.167~7.204(m,3H),7.448(d,2H,J=8Hz).
13C NMR(125MHz,CDCl3)δ(ppm):14.4,20.1,33.5(2C),34.1(2C),37.0,39.7,44.7,80.3,97.7,113.2,119.4,120.8,121.8,127.1(2C),127.6,131.8(2C),143.0,147.5(d,J=250Hz),149.5,151.1(J=250Hz).
MS m/z(RI,%):395.2(M+,100),297.0(41).
DSC:C81.6 N 256.5I。
采用相同的合成方法,制备得到如下表5所列化合物:
表5
实施例3:
该实施例为4-正丁基-4'-((2,3-二氟-4-异硫氰酸酯基苯基)乙炔基)-1,1'-联苯的合成:
用4'-正丁基-4-乙炔基联苯替代实施例1中的4-正戊基苯乙炔,其他操作采用与实施例1同样的合成方法,得到4-正丁基-4'-((2,3-二氟-4-异硫氰酸酯基苯基)乙炔基)-1,1'-联苯。
结构鉴定数据如下:1H NMR(500MHz,CDCl3)δ(ppm):0.940(t,3H,J=7.5Hz),1.356~1.401(m,2H),1.593~1.645(m,2H),2.641(t,2H,J=8Hz),6.879(d,1H,J=8Hz),7.180(d,1H,J=8Hz),7.245(d,2H,J=8Hz),7.496(d,2H,J=8Hz),7.567(s,4H).
13C NMR(125MHz,CDCl3)δ(ppm):14.0,22.5,33.6,35.4,81.5,97.4,113.0,120.6,120.9,122.0,126.9(2C),126.9(2C),127.6,129.0(2C),132.2(2C),137.4,141.9,142.9,143.1,147.5(d,J=250Hz),151.1(J=250Hz).
MS m/z(RI,%):403.1(M+,79),360.1(100).
DSC:C 61.9S 197.4N 250.2I。
采用相同的合成方法,制备得到如下表6所列化合物:
表6
实施例4:
液晶组合物,其组分结构与质量比例和性能数据如下表7所示。
表7
实施例4液晶组合物具有较高的双折射率、极低的旋转粘度,以及极低的旋转粘度和弹性常数比。
实施例5:
液晶组合物,其组分结构与质量比例和性能数据如下表8所示。
表8
实施例5液晶组合物具有较高的双折射率、极低的旋转粘度,以及极低的旋转粘度和弹性常数比。
实施例6:
液晶组合物,其组分结构与质量比例和性能数据如下表9所示。
表9
实施例6液晶组合物具有较高的双折射率、极低的旋转粘度,以及极低的旋转粘度和弹性常数比。
实施例7:
液晶组合物,其组分结构与质量比例和性能数据如下表10所示。
表10
实施例7液晶组合物具有较高的双折射率、极低的旋转粘度,以及极低的旋转粘度和弹性常数比。同时,在高频19GHz下,具有大介电各向异性的优点。
对比例1:
现有的苯环侧向氟原子的异硫氰酸酯液晶化合物(化合物a~d),结构式如下所示:
以上化合物a~b以及本发明实施例1,用DSC进行液晶相变温度测试,结果如下表11所示:
表11
从上表可以看出,与对比例1中化合物a~d相比,本发明通过在苯环2,3-位引入侧向氟原子取代基,不仅具有互变液晶相,而且具有最高的清亮点。这表明本发明液晶化合物在分子中苯环特定位置的氟取代后,取得了意想不到的技术效果:实现了液晶相性能的大幅度提升,超过现有已知类似结构的液晶化合物。
对比例2:
液晶组合物,由下表12所示的已知的单氟取代异硫氰酸酯液晶组成:
表12
可以看出,本发明实施例7的液晶组合物,与对比例2具有相类似的结构和组分比例。本发明实施例7较对比例2液晶清亮点提升28.3℃;本发明实施例7低温长期存储温度(LTS)达到-10℃,较对比例2扩展了20℃;实施例7较对比例2的液晶工作温区扩展48℃;并具有更高的双折射率,同时γ1/K11值也大幅度降低。
Claims (15)
1.一种含2,3-二氟取代苯的异硫氰酸酯液晶化合物,其特征在于,所述化合物的结构如通式Ⅰ所示:
其中:
R为碳原子数为1~10的烷基、氢被氟取代的烷基、烷氧基或氢被氟取代的烷氧基;或者为碳原子数为2-10的烯基、氢被氟取代的烯基、烯氧基或氢被氟取代的烯氧基;或者为碳原子数为3-8的环烷基、氢被氟取代的环烷基、含环烷基取代的烷基或氢被氟取代的含环烷基取代的烷基;
Z1为单键、-C≡C-、-CH=CH-、-CF=CF-或-CH2CH2;
Z2为单键、-C≡C-、-CH=CH-、-CF=CF-或-CH2CH2;
其中Z1和Z2至少有一个是选自-C≡C-、-CH=CH-、-CF=CF-或-CH2CH2;
环A为苯环、环己烷、环己烯或氢被氟、氯、甲基或/和乙基取代的苯环;n=0,1或2;
环B为苯环、环己烷、环己烯或氢被氟、氯、甲基或/和乙基取代的苯环。
2.根据权利要求1所述的液晶化合物,其特征在于,n=0。
3.根据权利要求1所述的液晶化合物,其特征在于,n=1,环A为苯环或环己烷。
4.根据权利要求1所述的液晶化合物,其特征在于,n=2,环A为苯环或环己烷。
5.根据权利要求1所述的液晶化合物,其特征在于,所述化合物结构式为Ⅰ-1~Ⅰ-8式中任一结构式所示;
6.权利要求1所述的含2,3-二氟取代苯的异硫氰酸酯液晶化合物的合成方法,其特征在于,方法包括:
(1)2,3-二氟苯胺与卤化试剂反应,得到4-卤素取代-2,3-二氟苯胺;
(2)4-卤素取代-2,3-二氟苯胺在过渡金属催化下与芳基硼酸衍生物或含末端炔基的衍生物进行偶联反应,得到联苯胺类中间体或炔基苯胺类中间体;
(3)联苯胺类中间体或炔基苯胺类中间体进行光气化反应得到异硫氰酸酯类液晶化合物。
7.根据权利要求6所述的合成方法,其特征在于,步骤(1)中卤化试剂选自碘、溴或N-溴代丁二酰亚胺。
8.根据权利要求6所述的合成方法,其特征在于,所述的过渡金属催化剂选自含钯的配合物或镍的配合物。
9.一种液晶组合物,其特征在于,包含结构通式Ⅰ所示的一种或多种结构不同的液晶化合物。
10.根据权利要求9所述的液晶组合物,其特征在于,结构通式Ⅰ所示的液晶化合物的质量百分比含量为10~100%;小于100%时,其余组分包含选自一种或多种结构通式Ⅱ所示的液晶化合物;
其中,R1为碳原子数为1~10的烷基、烷氧基、氟化烷基;或者为,碳原子数为2-10的烯基、烯氧基、氟化烯基、氟化烯氧基;或者为,碳原子数为3-8的环烷基或含环烷基取代的烷基;环C为苯环、环己烷或环己烯;m=0,1;n=0,1;X1,X2,X3为氢或氟。
11.根据权利要求10所述的液晶组合物,其特征在于,结构通式Ⅱ选自以下Ⅱ-1~Ⅱ~12所示的液晶化合物:
12.根据权利要求9所述的液晶组合物,其特征在于,所述液晶组合物包含式I-1所示的液晶化合物。
13.根据权利要求11所述的液晶组合物,其特征在于,I-1所示的液晶化合物的质量百分比含量大于等于40%。
14.权利要求1所述化合物用于制备液晶光学元件或微波组件的应用。
15.液晶光学元件或微波组件,其特征在于,所述液晶光学元件或微波组件中包含权利要求9所述的液晶组合物。
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