CN1179153A - 液晶化合物 - Google Patents
液晶化合物 Download PDFInfo
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- CN1179153A CN1179153A CN96192800A CN96192800A CN1179153A CN 1179153 A CN1179153 A CN 1179153A CN 96192800 A CN96192800 A CN 96192800A CN 96192800 A CN96192800 A CN 96192800A CN 1179153 A CN1179153 A CN 1179153A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 20
- 125000006850 spacer group Chemical group 0.000 claims abstract description 11
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000004990 Smectic liquid crystal Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
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- 125000005466 alkylenyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 150000007516 brønsted-lowry acids Chemical class 0.000 description 1
- 150000007528 brønsted-lowry bases Chemical class 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- -1 nAcyl chlorides Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
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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
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
- C09K19/2021—Compounds containing at least one asymmetric carbon atom
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Abstract
式Ⅰ的液晶化合物X(－Y－A－Y－M－Y－B)n(Ⅰ)其中X为一n价脂肪族,芳香族或环脂肪族基团,或为一n价链烯基或炔基;n为2,4或5;每个Y彼此独立,可为直接键,－COO－,－OCO－,－O－,－CONH－或－CON(R)－,其中R为C1－C4烷基;A为一间隔基;M为一液晶基元基团和B为一侧链。此液晶化合物特别适于信息显示。
Description
目前大量的液晶化合物已为人知。然而，这些化合物通常不能以玻璃体方式固化。具有液晶性，且可以玻璃体方式固化的确定化合物例如在专利DE-A 3703640，DE-A 3827603，DE-A 3830968和EP-A-504 660中已有描述，在前三个申请中，所描述的化合物存在一个共同特征：其容易结晶，甚至是从玻璃态。这样在凝固态的取向也就不稳定。由于在晶体中形成混晶对分子的要求比在各向异性流体中混合的要求要强烈的多，在这种结晶情况下，所采用的任何混合物也不再稳定。
专利EP-A-504 660所描述的化合物可形成稳定的玻璃体，其拥有与分子长轴平行的高偶极矩，并可形成向列型或近晶型A相，由于沿着分子长轴的偶极矩，这些物质在电场中平行取向，其因此不具备铁电性，同时在电场中所显示的任何螺旋超级结构均不稳定。
此外，所知的液晶体系有一个确定的结构，其中液晶基元(mesogen)基团通过一个间隔基与中心单元相连(如专利DE-A-40 118117)然而这些物质并不能以玻璃体方式固化，但相应地由于其高对称性，结晶极易发生。此外，
液晶(Liquid crystals 11(5)(1992)，779)描述了一种通过间隔基与中心单元相连的铁电性液晶，这些物质具有对热、弱酸或碱、水不稳定的液晶基元结构。
期望作为液晶铁电性材料的化合物，其应为那些物质：有一个相特性，在经过冷却过程所表现的相序为向列型、近晶型A和近晶型C。同时为防止显示表现出压敏性，材料应有高粘流性，而且尤其应对弱酸和碱稳定。此外，更高的期望特征是具有与其他液晶化合物好的混合性。
本发明的目的是提供全新的液晶混合物，其可以以玻璃体方式固化，具有近晶和向列相。对温度和PH的变化、水不敏感，且有高的粘流性。
我们已发现这一目的可用式I的化合物来实现：
X(-Y-A-Y-M-Y-B)n I
其中，X为一n价脂肪族、芳香族或环脂肪族基团或为一n价链烯基或炔基，
n为2，4或5
每个Y彼此独立，可为直接键、-COO-、-OCO、-O-、-CONH，或-CON(R)-，其中R为C1-C4烷基，
A为一间隔基，
M为一液晶基元基团，
且B为一侧链。
X基团的实例有：亚烷基，
-CH＝CH-，-C≡C-，
或可被O，NH或NR间断的亚烷基，
各个亚烷基的实例：
-(CH2)p-，
-CH2OCH2-，-CH2NHCH2-或
其中p为1-20，优选1-10，R在这里有特定的说明，
n优选2或4。
至于Y基团，尤其优选-OCO-，-O-，和-COO-，
可采用的间隔基均为那些已知用于此目的基团，间隔基通常通过酯或醚基或直接键与X相连。间隔基通常有2-30，优选2-12，尤其为6-12个碳原子，且可被例如O，S，NH或NCH3间断。间隔链的合适取代基为氟、氯、溴、氰基、甲基和乙基。
代表性的间隔基实例为：(-CH2)p-，-(CH2CH2O)mCH2CH2-，-CH2CH2SCH2CH2-，-CH2CH2NHCH2CH2-，
其中，m为1-3，p为1-12。
M可为一已知的液晶基元基团，尤其适合的为包含芳族或杂芳族基团的基团，尤其是液晶基元基团符合式III：
(-T-Y1)r-T III
其中，每个T彼此独立，可为一芳香或杂芳基团
每个Y1彼此独立，可为-O-，-COO-，-OCO-，-CH2O-，-OCH2-，-CH＝N-或-N＝CH2-，或直接键
r为1-3，r优选1或2，
Y1优选-COO-，-OCO-，或直接键。
T通常为一芳香碳环或杂环体系，可为F、Cl、Br、CN、OH或硝基取代，例如符合以下基本结构：
尤其优选的液晶基元基团M的实例为：
侧链B的实例为C2-C30烷基或链烯基，优选C2-C11烷基或链烯基，其中基团可为线性或支化的，可一次或多次为-O-，-OCO-，-COO-，
-NH-或-N(CH3)-间断，也可为苯基，F、Cl、Br、CN或OH取代。
B尤其优选经-O-，-COO-或-OCO-连接的C3-C11烷基，且可一次或多次为O间断，优选非支化的。
各个B基团的实例为：
-C2H5，-C3H7，-C4H9，-C5H11，-C6H13，
-C7H15，-C8H17，-C9H19，-C10H21，-C11H23，-C12H25，
-CH2CH＝CH2，-(CH2)7CH＝CH2或-(CH2)8CH＝CH2.
其他的优选合适的侧链B为经-O-，-COO-或-OCO-连接的手性C3-C11烷基，其可为F、Br、Cl、CN或OH取代，或可为-O-，-COO-，-OCO-，或
间断。
手性侧链B的实例为
其中R1为C1-C12烷基，可为手性或非手性，R2可为基团R1，F，Cl。
优选的R1基团实例为：
-CpH2p+1
其中，p为1-12。
在式I的化合物中，与X相邻的桥元Y为-COO-、-CONH，或-CONR，为了制备这种化合物，分子式为X(COCl)n的酰氯可与下式的化合物
HO-A-Y-M-Y-B，
H2N-A-Y-M-Y-B或
以本来已知的方法反应。如果与X相邻的Y为桥元-OCO-，则分子式为X(OH)n的化合物可类似地与下式的化合物反应，
如果桥元Y为O，则羟基与卤代烷基反应。
-般的制备方法可从文献中获悉，值得一提的一个实例为用二环己基碳化二亚胺(DCC)反应制备酯，反应的详细情况在实例中给出，其中的份额与百分比除特别说明外均以重量计。
式I的化合物为液晶化合物，且依据结构不同，可形成近晶相，向列相或胆甾相。其适合于液晶化合物通常所应用的所有目的。
全新的化合物处于低分子量与聚合的液晶化合物间的中间位置，与聚合物相比，其可重复制备，具有真正统一的结构，然而却有聚合物的粘度。
为了得到期望的性质，利用式I的化合物的混合物是有利的，可就地制备，即合成时或通过机械混合制备这些混合物。
新化合物可单独地，相互混合地或与其他液晶一起用在光学信息显示装置中，其尤其适合用于显示和生产反光涂层。
实施例：
实施例中采用的一些缩写如下：
K：结晶相
I：各向同性相
Sc：液晶基元呈铁电性排列的近晶C相
Sa：近晶A相
*：手性液晶相
Z：包含X和Y基团的中心单元
S：未详细表征的近晶相
相转变温度用偏光显微镜来记录，在Mettler FP 80/82显微镜加热阶段进行温度控制，自极化采用Miyasato等提出的方法测定(日本应用物理杂志(Jpn.J.Appl.Phys.22(1986)，L230)
实施例1
制备(2-庚基-5-〔4-(8-羟基辛氧基)苯基-1，3，4-噻二唑)对苯二甲酸二酯
0.02mol 1，4-对苯二酰氯溶于150ml甲苯中，加热至沸腾，经1小时滴入由0.022mol 2-庚基-5-〔4-8-羟基辛氧基〕苯基-1，3，4-噻二唑溶于包含0.2mol吡啶和50ml甲苯的混合液中形成的溶液。反应完毕后，将混合物蒸干，用柱层析纯化(硅胶，甲苯/乙酸乙酯＝3/1)，产物用甲苯/乙醇重结晶，产率：13.2g，70％，相特性：K1171。
实施例2-14采用与实施例1类似的方法制备，若表中显示组(-A-Y-M-Y-B)是混合物，则相应摩尔量的HO-A-Y-M-Y-B化合物的混合物在合成中被采用，并产生化合物I的统计混合物。 
实施例15
制备苯四酸四(2-庚基-5-〔4-(羟基辛氧基)苯基-1，3，4-噻二唑〕酯
a)苯四酸酐与2-庚基-5-〔4-(8-羟基辛氧基)苯基-1，3，4-噻二唑的反应
21.8g(0.1mol)苯四酸酐溶于150ml二甲基甲酰胺(DMF)中，混合物加热至110℃，84.8g(0.21mol)2-庚基-5-〔4-(8-羟基辛氧基)苯基-1，3，4-噻二唑溶于50ml DMF中形成的溶液搅拌条件下于半小时内滴加完毕，混合液在110℃再搅拌2小时，反应混合物搅拌下小心地用水来沉淀，抽滤反应产物，并加入饱和碳酸钠溶液中未溶解的部分被滤出，反应产物然后用稀HCl沉淀，抽滤，用乙醇洗涤，并用甲苯/乙醇重结晶，产率66.7g(65％)。
b)来自实施例15a的反应产物与亚硫酰氯的反应
为了制备二酰氯，51.3g(0.05mol)实施例15a的反应产物与100ml亚硫酰氯混合，混合物在50℃搅拌3小时，当气体逸出完全，亚硫酰氯被减压脱去，固体用石油醚洗涤，酰氯在40℃减压干燥，产率50.5g(95％)。
c.标题化合物的制备
0.53g(0.0005mol)酰氯分散于50ml绝对甲苯中，加热至40℃，0.44g(0.0011mol)2-庚基-5-〔4-(8-羟基辛氧基)苯基-1，3，4-噻二唑溶于50ml甲苯和30ml吡啶中，并滴加至上述溶液，反应用薄层色谱来鉴视。当反应完全，反应混合物用水沉淀，用柱层析(硅胶60，甲苯/乙酸乙酯4∶1)来纯化。
产率：0.57g(64％)
相特性：Sa 87I(至室温无结晶)以下化合物以类似方法制备：
Claims (11)
1.一种式I的液晶化合物
X(-Y-A-Y-M-Y-B)nI
其中，X为一个n价脂肪族，芳香族或环脂族基团，或为一个n价链烯基或炔基，
每个Y彼此独立，可为直接键，-COO-，-OCO-，-O-，-CONH-，或-CON(R)-，其中R为C1-C4烷基，
A为间隔基，
M为一液晶基元基团，B为一侧链。
2.如权利要求1所要求的式I的液晶化合物，其中n为2或4。
3.如权利要求1所要求的式I的液晶化合物，其中Y为-O-，-COO-或-OCO-。
4.如权利要求1所要求的式I的液晶化合物，包含的间隔基有2-12个碳原子。
5.如权利要求1所要求的式I的液晶化合物，其中M为
(T-Y1)r-T
其中，T彼此独立，可为芳香或杂芳基团，
每个Y1彼此独立，可为-O-，-COO-，-OCO-，-CH2O-，-OCH2-，-CH＝N-或-N＝CH-，或直接键和
r为1-3。
6.如权利要求1所要求的式I的液晶化合物，
其中B为可被-O-，-OCO-，-COO-，
-NH-，-N(CH3)-间断并可为苯基，F，Cl，Br，CN，OH取代的C2-C11烷基或链烯基。
7.如权利要求5所要求的液晶化合物，其中Y1为-COO-，-OCO-，或直接键。
8.如权利要求6所要求的液晶化合物，其中B为经-O-，-COO-或-OCO-连接的C3-C11烷基，并可一次或多次为O间断和优选非支化。
9.如权利要求6所要求的液晶化合物，其中B为经-O-，-COO或-OCO-连接的手性C3-C11烷基，可为F、Cl、Br、CN或OH取代，或可被O，COO，OCO或
间断。
10.如权利要求9所要求的液晶化合物，其中B为经O，COO或OCO连接的手性C3-C11烷基，其可为F，Cl，Br或OH取代，或可被O或COO间断。
11.如权利要求1-10中任何一项所要求的化合物单独地，相互混合地或与其他液晶一起用于光学信息显示的装置中。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| WOPCT/EP95/01113 | 1995-03-24 | ||
| PCT/EP1995/001113 WO1996030351A1 (de) | 1995-03-24 | 1995-03-24 | Flüssigkristalline verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1179153A true CN1179153A (zh) | 1998-04-15 |
Family
ID=8165982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96192800A Pending CN1179153A (zh) | 1995-03-24 | 1996-03-22 | 液晶化合物 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0815094A1 (zh) |
| JP (1) | JPH11504001A (zh) |
| KR (1) | KR19980703220A (zh) |
| CN (1) | CN1179153A (zh) |
| WO (2) | WO1996030351A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079862A (zh) * | 2020-10-29 | 2020-12-15 | 江苏创拓新材料有限公司 | 一种碳酸脂类液晶中间体及其制备方法和应用 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19630068A1 (de) * | 1996-07-25 | 1998-01-29 | Basf Ag | Neue flüssigkristalline Verbindungen und deren Vorprodukte |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3608764A1 (de) * | 1985-03-22 | 1986-10-02 | Merck Patent Gmbh, 6100 Darmstadt | Carbocyclische verbindungen |
| DE4108627A1 (de) * | 1991-03-16 | 1992-09-17 | Basf Ag | Fluessigkristalline verbindungen |
| DE4224083A1 (de) * | 1992-07-22 | 1994-01-27 | Basf Ag | Definierte, oligomere flüssigkristalline Verbindungen mit smektisch flüssigkristallinen Phasen |
| DE4332733A1 (de) * | 1993-09-25 | 1995-03-30 | Basf Ag | Flüssigkristalline Verbindungen |
-
1995
- 1995-03-24 WO PCT/EP1995/001113 patent/WO1996030351A1/de active Application Filing
-
1996
- 1996-03-22 CN CN96192800A patent/CN1179153A/zh active Pending
- 1996-03-22 KR KR1019970706624A patent/KR19980703220A/ko not_active Application Discontinuation
- 1996-03-22 WO PCT/EP1996/001285 patent/WO1996030352A1/de not_active Application Discontinuation
- 1996-03-22 JP JP8528909A patent/JPH11504001A/ja active Pending
- 1996-03-22 EP EP96908125A patent/EP0815094A1/de not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112079862A (zh) * | 2020-10-29 | 2020-12-15 | 江苏创拓新材料有限公司 | 一种碳酸脂类液晶中间体及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11504001A (ja) | 1999-04-06 |
| WO1996030351A1 (de) | 1996-10-03 |
| WO1996030352A1 (de) | 1996-10-03 |
| KR19980703220A (ko) | 1998-10-15 |
| EP0815094A1 (de) | 1998-01-07 |
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